2-Hydrocarbyloxy-pyridine compounds

ABSTRACT

Compounds of the formula ##SPC1## 
     Wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR 1 , --COR 2 , ##EQU1## --SO 2  R 2 , ##EQU2## --CN, --NH 2 , --NO, --NO 2  or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z 1  is cyano, ##EQU3## --NH--OR 10 , ##EQU4## --OR 12 , --SR 12  or --SO 2  R 12  and Z 2  is chlorine, bromine, cyano, hydroxy, mercapto, --OR 12 , --SR 12 , --SO 2  R 12 , ##EQU5## --NH--OR 10  or ##EQU6## R 1  is aliphatic; R 2  is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R 3  and R 4  when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R 3  and R 4  when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R 5  and R 6  when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R 5  and R 6  when taken together with the nitrogen atom to which they are attached are heterocyclic; R 7  is hydrogen, aliphatic or aromatic; R 8  and R 9  are aliphatic or aromatic, R 10  is hydrogen, aliphatic or aralkyl, R 11  is aliphatic and R 12  is aliphatic, aromatic or aralkyl; R 10  and R 11  when taken together with the nitrogen atom to which they are attached are heterocyclic.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a division of application Ser. No. 372,024 filed June 21, 1973.

This invention relates to compounds of the formula ##SPC2##

Wherein X is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, heteroaryl having four to seven carbon atoms and containing one or two heteroatoms selected from the group of O, N and S, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined or hydrogen; Y is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined, --COOR₁, --COR₂, ##EQU7## --SO₂ R₂, ##EQU8## --CN, --NH₂, --NO, --NO₂ or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z₁ is cyano, ##EQU9## --NH--OR₁₀, ##EQU10## --OR₁₂, --SR₁₂ or --SO₂ R₁₂ and Z₂ is chlorine, bromine, cyano, hydroxy, mercapto, --OR₁₂, --SR₁₂, --SO₂ R₁₂, ##EQU11## --NH--OR₁₀ or ##EQU12## R₁ is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms or one of said radicals substituted as hereinafter defined; R₂ is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl, phenethyl, pyridyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or pyrrolyl, one of said radicals substituted as hereinafter defined; R₃ and R₄, when taken separately, are alkyl having one to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined or hydrogen; R₃ and R₄, when taken together with the nitrogen atom to which they are attached, form a piperidino, piperazino, morpholino, or ethyleneimino radical; R₅ and R₆, when taken separately, are alkyl having one to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl benzyl, phenethyl, pyridyl, thi-azolyl, benzothiazolyl, imidazolyl, bemzimidazolyl, pyrrolyl, one of said radicals substituted as hereinafter defined or hydrogen; R₅ and R₆ when taken together with the nitrogen atom to which they are attached, form a piperidino, piperazino, morpholino or ethyleneimino radical; R₇ is hydrogen, alkyl having one to six carbon atoms, phenyl or phenyl substituted as hereinafter defined; R₈ and R₉ are alkyl having one to six carbon atoms, phenyl or phenyl substituted as hereinafter defined; R₁₀ is alkyl having one to six carbon atoms, benzyl, phenethyl, one of said groups substituted as hereinafter defined or hydrogen; R₁₁ is alkyl having one to six carbon atoms or said alkyl substituted as hereinafter defined; R₁₂ is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl, phenethyl or one of said radicals substituted as hereinafter defined; the substituents for substituted alkyl or alkenyl radicals specified hereinabove being selected from the group consisting of cyano, hydroxy, acetoxy, phenoxyacetoxy, alkoxy having one to two carbon atoms, phenoxy, monoalkylamino having one to four carbon atoms, dialkylamino having one to four carbon atoms in each alkyl moiety, N-ethylcarbamoyloxy, N-methylcarbamoyloxy, N-phenylcarbamoyloxy, acetylamino, benzoylamino, heteroaryl having four to seven carbon atoms and containing one or two heteroatoms selected from the group of O, N and S, and ##EQU13## wherein Z constitutes the atoms completing a morpholino, piperidino, piperazino, N-methyl-piperazino or cyclopentamethyleneimino group and the substituents for the substituted cycloalkyl, phenyl, benzyl, phenethyl and heterocyclic radicals specified hereinabove being selected from the group consisting of bromine, chlorine, cyano, alkyl having one to three carbon atoms and alkoxy having one to two carbon atoms. The above-mentioned heteroaryl residues having four to seven carbon atoms may be pyridyl, thiazolyl, benzthiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or pyrrolyl groups.

The starting materials for the preparation of the novel compounds of formula I are 2,6-dihydroxypyridine derivatives of the formula: ##SPC3##

wherein X and Y have the above-stated meaning. These starting compounds may be prepared in a known manner analogous to the method described by Bobbitt and Scola, Journ. of Org. Chem. 25, 560, by the condensation of correspondingly substituted acetic acid amides with correspondingly substituted β-ketocarboxylic acid esters. They may also be prepared in accordance with various other processes, as described for example in the monograph "Heterocyclic Compounds Pyridine and its Derivatives Part. 3" by Klingsberg. This monograph has appeared in the frame of the series published by Arnold Weissberger "The Chemistry of Heterocyclic Components," Interscience Publishers. The 2,6-dihydroxypyridine derivatives of formula II, according to Bobbitt and Scola, ibid., are converted by means of phosphoroxychloride or analogously by means of phosphoroxybromide at 180°C. into the corresponding 2,6-dichloro or 2,6-dibromopyridine derivatives of formula III: ##SPC4##

wherein X and Y have the above-stated meanings and Hal is bromine or preferably chlorine.

For the preparation of compounds of formula I, wherein Z₂ stands for chlorine or bromine and to which formula Ia then pertains, a compound of formula III is reacted with a compound of formula IV in accordance with the reaction: ##SPC5##

Q in this instance is hydrogen or a metal, preferably an alkali metal such as sodium or potassium. In the event that Z₁ stands for --SO₂ R₁₂, zinc is especially preferred.

Reaction (1) is carried out in equimolar ratio at temperatures of 20°-100°C. in a suitable inert solvent. The exchange of the chlorine or bromine atom in the 6-position is ascertained by analysis of the NMR absorption of the obtained compounds of formula Ia.

To the extent that in formula IV, Z₁ stands for the radicals: ##EQU14## --NH--OR₁₀ or ##EQU15## hydrogen is appropriately selected for Q, i.e., in the reaction equation (1) formula IV then stands for the compounds ##EQU16## H₂ NOR₁₀ or ##EQU17## In this instance, the reaction is carried out in accordance with reaction equation (1), preferably in the temperature range of 20° to 50°C. and as suitable inert solvents, alkanols with a chain length of one to four carbon atoms are preferably used. In those instances where the physical properties are appropriate, an excess of one of the reaction constituents may also serve as the solvent.

To the extent that in formula IV, Z₁ stands for cyano or for --SO₂ R₁₂, a metal is appropriately selected for Q, preferably an alkali metal such as sodium or potassium and in the event that Z₁ is SO₂ R₁₂, zinc is particularly preferred. In reaction equation (1), formula IV then stands for the compounds NaCN, KCN and Zn(SO₂ R₁₂)₂. In this instance, the reaction in accordance with reaction equation (1) is carried out preferably in the temperature range of 60°-80°C. in a suitable organic solvent such as an alcohol, ether, ester, carboxylic acid amide, N-substituted carboxylic acid amide such as dimethylformamide, dialkylsulfoxide such as dimethylsulfoxide or dialkylsulfone, all of these preferably having not more than six carbon atoms. In the reaction of sulfinates, the addition of a copper-I-salt is advantageous.

To the extent that in formula IV, Z₁ stands for the radicals --OR₁₂ or --SR₁₂, a metal atom is selected for Q, preferably an alkali metal atom such as sodium or potassium. In reaction equation (1), formula IV then stands for the compounds NaOR₁₂, NaSR₁₂, KOR₁₂ and KSR₁₂. In this instance, the reaction is conducted in accordance with reaction equation (1), preferably in the temperature range of 60°-100°C., in an inert organic solvent, e.g., an aromatic hydrocarbon such as benzene, toluene or xylene, or in an excess of the reaction constituent HOR₁₂ or HSR₁₂ as the solvent.

The compounds of formula Ia may be further reacted in accordance with the reaction: ##SPC6##

This reaction is carried out at temperatures of 20°-200°C. in a suitable solvent. The molar ratio of reactants is 1:1.

When Z₂ is OH in the compound of formula V, there is used a suitable alkali metal hydroxide such as sodium hydroxide or potassium hydroxide in an aqueous or aqueous-alcoholic medium. However, sodium carbonate, potassium hydroxide or similar compounds which release hydroxyl ions in an aqueous medium may also be used. The solvents may be alkanols having one to four carbon atoms. The preferred temperature range is 70°-150°C.

If Z₂ is --SH in the compound of formula V, an alkali metal hydrosulfide, preferably NaSH or KSH, is used and the reaction is carried out in an aqueous medium, preferably at temperatures of 100°-150°C.

In the event Z₂ stands for --OR₁₂ or --SR₁₂, an alkali metal, preferably sodium or potassium, is selected for Q in formula V and the reaction constituents are reacted at temperatures of 60°-150°C., preferably at 60°-100°C., in a suitable inert solvent, e.g., an aromatic hydrocarbon such as benzene, toluene or xylene, or in an excess of the reaction constituent HOR₁₂ or HSR₁₂ as solvent.

In the event Z₂ is cyano or --SO₂ R₁₂ in formula V, a metal is selected for Q, preferably an alkali metal such as sodium or potassium or when Z₂ is --SO₂ R₁₂, zinc is also useful. The reaction between these compounds of formulae Ia and V is carried out in a suitable organic solvent at temperatures of 20°-100°C. and preferably 60°-80°C. Suitable organic solvents, for example, include alcohols, ethers, esters, carboxylic acid amides, N-substituted carboxylic acid amides such as dimethylformamide, dialkylsulfoxides such as dimethylsulfoxide or dialkylsulfones, all having preferably not more than six carbon atoms. In the use of sulfinates, the addition of a copper-I-salt is advantageous.

In the event Z₂ is ##EQU18## --NH--OR₁₀ or ##EQU19## in formula V, hydrogen is selected for Q, and the constituents are reacted at 100°-200°C., preferably at 160°-180°C., in an inert solvent, preferably an alkanol having one to four carbon atoms or, in those instances where the physical properties are appropriate, an excess of one of the reaction constituents may be used as the solvent.

Novel compounds wherein Z₂ has the same meaning as Z₁ may be prepared in accordance with the reaction: ##SPC7##

wherein a compound of formula III is reacted with a compound of formula IV in a molar ratio of at least 1:2 in a suitable solvent at temperatures of 20° to 200°C. When Z₁ is ##EQU20## --NH--OR₁₀ or ##EQU21## in formula IV, hydrogen is selected for Q, and when Z₁ is --CN, --OR₁₂, --SR₁₂ or --SO₂ R₁₂, a metal is selected for Q, preferably in alkali metal such as sodium or potassium. Also when Z₁ is --SO₂ R₁₂, zinc is suitable. Suitable solvents are alcohols, ethers, hydrocarbons, etc. The selection of the solvent may be the same as described for reaction (1).

Novel compounds when Z₂ is --OH may also be prepared by the reaction of a 2-hydroxy-6-bromo- or 2-hydroxy-6-chloropyridine derivative of formula VI with a compound of formula IV in a molar ratio of 1:1 in accordance with reaction: ##SPC8##

The reaction is carried out in a suitable solvent at temperatures of 20° to 100°C. The data respecting the solvents and the meaning and selection of Q set forth above for reaction equations (1) and (3), apply to reaction (4).

Compounds of formula VI may be prepared by the reaction of the corresponding 2,6-dihydroxypyridine compounds with phosphoroxychloride or phosphoroxybromide at 80°-100°C. in an inert organic solvent such as benzene, toluene or xylene.

If reactions (1) through (4) are carried out at temperatures which are above the boiling point of a reaction constituent or of the solvent used, then the utilization of excess pressure is required.

Compounds of formulae Ia, Ib and Ic are preferred groups of novel compounds. Further preferred compounds are those wherein in formula I:

X is alkyl having one to three carbon atoms, preferably methyl,

Y is cyano,

Z₁ is cyano, alkoxy having one to two carbon atoms, alkylsulfonyl having one to two carbon atoms, amino, monoalkylamino having one to three carbon atoms or monoalkylamino having one to three carbon atoms and substituted by alkoxy having one to two carbon atoms and

Z₂ is cyano, hydroxyl, alkoxy having one to two carbon atoms, alkylsulfonyl having one to two carbon atoms, amino, monoalkylamino having one to three carbon atoms or monoalkylamino having one to three carbon atoms and substituted by alkoxy having one to two carbon atoms.

Such preferred compounds are especially the pyridine compounds of the formulae: ##SPC9##

It is possible that the novel compounds of formula I in part exist in tautomeric forms. For example, the following tautomeric formulae are possible. ##SPC10##

As used herein, formula I is also understood to embrace such possible tautomers.

As the reaction constituents of formula III such as 2,6-dichloro or 2,6-dibromo pyridine derivatives are suitable, for example, which in the X position contain hydrogen or a methyl, ethyl, n-propyl, isopropyl, vinyl, α-methylvinyl, n-butyl, isobutyl, sec.-butyl, n-amyl or isoamyl, n-hexyl, 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-morpholinoethyl, 2-piperidinoethyl, 2-pyrrolidinoethyl, N-methyl-N'-piperazinoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-acetoxyethyl, 2-phenoxyacetoxyethyl, N-ethylcarbamoyloxyethyl, N-phenylcarbamoyloxyethyl, 2-phenoxyethyl, 3-methoxypropyl, cyclohexyl, benzyl, 3-methylbenzyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,5-dimethyl-4-chlorophenyl or the following radicals: ##SPC11##

The compounds of formula III may, in the Y position, contain for example hydrogen, cyano, amino, nitroso, nitro, methyl, ethyl, 2-hydroxyethyl, 2-cyanoethyl, 2-acetoxyethyl, 2-benzoyloxyethyl, 2-methoxyethyl, 2-phenoxyethyl, 2-monoethylaminoethyl, 2-monomethylaminoethyl, 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-morpholinoethyl, 2-piperidinoethyl, 2-pyrrolidinoethyl, n-propyl, isopropyl, vinyl, α-methylvinyl, n-butyl, isobutyl, sec.-butyl, n-amyl, isoamyl, n-hexyl, cyclohexyl, benzyl, phenyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec.-butyloxycarbonyl, n-amyloxycarbonyl, n-isoamyloxycarbonyl, n-hexyloxycarbonyl, acetyl, acryloyl, propionyl, capronyl, capryl, hexahydrobenzoyl, phenacetyl, benzoyl, 4-methylbenzoyl, 2,4-dimethylbenzoyl, 4-methoxybenzoyl, 4-chlorbenzoyl, aminocarbonyl, monomethylaminocarbonyl, dimethylaminocarbonyl, ethyleniminocarbonyl, monoethylaminocarbonyl, monoisopropylaminocarbonyl, diethylaminocarbonyl, monooxethylaminocarbonyl, mono-γ-methoxypropylaminocarbonyl, morpholinocarbonyl, piperidinocarbonyl, cyclohexylaminocarbonyl, benzylaminocarbonyl, anilinocarbonyl, 4-methylanilinocarbonyl, N-methylanilinocarbonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec.-butylsulfonyl, n-amylsulfonyl, isoamylsulfonyl, n-hexylsulfonyl, benzylsulfonyl, phenylsulfonyl, 4-methylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 4-methoxyphenylsulfonyl, 4-chlorphenylsulfonyl, aminosulfonyl, monomethylaminosulfonyl, dimethylaminosulfonyl, ethyleniminosulfonyl, monoethylaminosulfonyl, monoisopropylaminosulfonyl, diethylaminosulfonyl, monooxethylaminosulfonyl, mono-γ-methoxypropylaminosulfonyl, morpholinosulfonyl, piperidinosulfonyl, cyclohexylaminosulfonyl, benzylaminosulfonyl, anilinosulfonyl, 4-methylanilinosulfonyl, N-methylanilinosulfonyl or the radicals ##SPC12## ##SPC13##

Of course, suitable starting compounds of formula III are also such 2,6-dichloro or 2,6-dibromopyridine derivatives which are identically substituted in the X and Y position, the preferred substituents being those which were indicated above for the X position.

Suitable reaction constituents ##EQU22## of formulae IV and V include, for example, the following primary and secondary amines and diamines:

Primary Amines

Ammonia, methylamine, ethylamine, 2-hydroxyethylamine, 2-methoxyethylamine, 3-phenoxyethylamine, 3-cyanoethylamine, n-propylamine, isopropylamine, 3-hydroxypropylamine-(1), 3-methoxypropylamine-(1), 3-isopropoxypropylamine-(1), 3-cyanopropylamine-(1), allylamine, 1-methallylamine, 2-methallylamine, n-butylamine, isobutylamine, sec.-butylamine, tert.-butylamine, 2-amino-2-methylpropanol-(1), crotylamine, 3-aminopentane, n-amylamine, isoamylamine, n-hexylamine, cyclohexylamine, benzylamine, 2-phenylethylamine, aniline, 4-methylaniline, 4-methoxyaniline, 2,4-dimethylaniline, 1-aminonaphthaline, 2-aminonaphthaline, ##SPC14##

and ##SPC15##

Secondary Amines

Dimethylamine, diethylamine, N-(2-cyanoethyl)-N-(2-hydroxyethyl)-amine, N-di-(2-hydroxyethyl)-amine, N-di-(2-cyanoethyl)-amine, N-methyl-(2-hydroxyethyl)-amine, N-isopropyl-(2-hydroxyethyl)-amine, N-n-butyl-(2-hydroxyethyl)-amine, N-cyclohexyl-(2-hydroxyethyl)-amine, N-benzyl-(2-hydroxyethyl)-amine, di-n-propylamine, di-isopropylamine, di-n-butylamine, diisobutylamine, di-n-amylamine, di-n-hexylamine, morpholine pyrrolidine, piperidine, N-methylpiperazine, N-methylcyclohexylamine, N-ethylcyclohexylamine, N-methylbenzylamine, N-methyl-3-methylbenzylamine, N-methylaniline, N-ethylaniline, N-2-hydroxyethylaniline, N-benzylaniline, N-methyl-2-chloraniline and N-ethyl-2-chloraniline.

Diamines

N-methyl-N',N'-dimethylhydrazine, N,N-dimethylhydrazine, N,N-diethylhydrazine, N-methyl-N-phenylhydrazine, N-aminopyrrolidine, N-aminopiperidine, N-aminopiperazine, N-aminomorpholine, N,N-dimethylethylenediamine, N,N-diethylethylenediamine, N,N-dimethylpropylenediamine-(1,3), or N,N-diethylpropylenediamine-(1,3), 2-morpholinoethylamine, 2-piperidinoethylamine, 2-pyrrolidinoethylamine and N-methyl-N'-3-amino-n-propylpiperazine of the formula: ##EQU23## Suitable reaction constituents H₂ NOR₁₀ or ##EQU24## according to the general formulae IV and V, for example, are:

Hydroxylamines ##SPC16##

As the hetarylamines for Z₁ and Z₂, the following may, for example, be used:

3-aminodiphenylene oxide

3-aminodiphenylene sulfide

3-aminodiphenylene sulfone

2-aminocarbazole

3-amino-N-methylcarbazole

3-amino-N-ethylcarbazole

3-amino-N-β-hydroxyethylcarbazole

3-amino-N-β-cyanoethylcarbazole

3-amino-N-n-propylcarbazole

3-amino-N-isopropylcarbazole

3-amino-N-(β-dimethylaminoethyl)-carbazole

3-amino-N-(β-diethylaminoethyl)-carbazole

3-amino-N-(γ-dimethylaminopropyl)-carbazole

3-amino-N-(α-methyl-β-dimethylaminoethyl)-carbazole

As the compounds HO--R₁₂ or HS--R₁₂, which after their conversion into the corresponding metal compounds, particularly the corresponding alkali metal compounds (especially the corresponding sodium and potassium compounds) are suitable as reaction constituents of formulae IV and V, the following alcohols, phenols or the corresponding mercaptans and thiophenols may be utilized: methanol, ethanol, 2-cyano-methanol-(1), ethylene glycol monomethyl ether, ethylene glycol monoethylether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butylether, ethylene glycol monophenyl ether, ethylene glycol monoxylenyl ether, diethylene glycol monomethylether, diethylene glycol monoethylether, diethylene glycol mono-n-butylether, triethylene glycol monomethylether, triethylene glycol monoethylether, triethylene glycol mono-n-butylether, n-propanol, isopropanol, propene-(1)-ol-(3), 2-methylpropene-(1)-ol-(3), n-butanol, sec.-butanol, isobutanol, tert.-butanol, 3-methoxybutanol-(1), 4-methoxybutanol-(1), butene-(1)-ol-(2), n-pentanol, isopentanol, n-hexanol, cyclohexanol, 4-methylcyclohexanol, 4-methoxycyclohexanol, phenylmethanol, (4-chlorophenyl)methanol, phenylethanol, (4-cyanophenyl)-ethanol, phenol, 2-methylphenol, 3-methylphenol, 4-methylphenol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 2-methoxy-3-methylphenol, 2-methoxy-4-methylphenol, 2-methoxy-5-methylphenol, 2-methoxy-6-methylphenol, 3-methoxy-5-methylphenol, 3-methoxy-6-methylphenol, 4-methoxy-5-methylphenol, 4-methoxy-6-methylphenol, 2,3-dimethoxyphenol, 2,4 -dimethoxyphenol, 3,5-dimethoxyphenol, 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2-bromophenol, 3-bromophenol, 4-bromophenol, 2-cyanophenol, 3-cyanophenol, 4-cyanophenol, 2,3-dichlorophenol, 2,4-dichlorophenol, 2,5-dichlorophenol, 2,6-dichlorophenol, 3,4-dichlorophenol, 3,5-dichlorophenol, 2,3-dibromophenol, 2,4-dibromophenol, 2,5-dibromophenol, 2,6-dibromophenol, 3,4-dibromophenol, 3,5-dibromophenol, 2-methyl-3-chlorophenol, 2-methyl-4-chlorophenol, 2-methyl-5-chlorophenol, 2-methyl-6-chlorophenol, 2-methyl-3-bromophenol, 2-methyl-4-bromophenol, 2-methyl-5-bromophenol, 2-methyl-6-bromophenol, 3-methyl-2-chlorophenol, 3-methyl-4-chlorophenol, 3-methyl-6-chlorophenol, 3-methyl-2-bromophenol, 3-methyl-4-bromophenol, 3-methyl-6-bromophenol, 4-methyl-5-chlorophenol, 4-methyl-6-chlorophenol, 4-methyl-5-bromophenol, 4-methyl-6-bromophenol, 4-chloropyrocatechol-1-methylether, 5-chloropyrocatechol-1-methylether, 4-bromopyrocatechol-1-methylether, 5-bromopyrocatechol-1-methylether, 4-chlororescorcinol-1-methylether, 4-chlororesorcinol-3-methylether, 4-bromoresorcinol-1-methylether, 4-bromoresorcinol-3-methylether, 2-chlorohydroquinone-1-methylether, 2-chlorohydroquinone-2-methylether, 5-chlororesorcinol-1-methylether, 1-naphthol, 2-naphthol, 2-methyl-1-naphthol, 3-methyl-1-naphthol, 4-methyl-1-naphthol, 7-methyl-1-naphthol, 3,6-dimethyl-1-naphthol, 3,7-dimethyl-1-naphthol, 4,6-dimethyl-1-naphthol, 4,7-dimethyl-1-naphthol, 6,7-dimethyl-1-naphthol, 4-methoxy-1-naphthol, 5-methoxy- 1-naphthol, 6-methoxy-1-naphthol, 7-methoxy-1-naphthol, 8-methoxy-1-naphthol, 2-chloro-1-naphthol, 3-chloro-1-naphthol, 4-chloro-1-naphthol, 5-chloro-1-naphthol, 7-chloro-1-naphthol, 8-chloro-1-naphthol, 2,3-dichloro-1-naphthol, 2,4-dichloro-1-naphthol, 5,7-dichloro-1-naphthol, 5,8-dichloro-1-naphthol, 2-chloro-4-bromo-1-naphthol, 2-bromo-1-naphthol, 3-bromo-1-naphthol, 4-bromo-1-naphthol, 5-bromo-1-naphthol, 6-bromo-1-naphthol, 7-bromo-1-naphthol 8-bromo-1-naphthol, 2-ethyl-4-bromo-1-naphthol, 2,4-dibromo-1-naphthol, 1-methyl-2-naphthol, 6-methyl-2-naphthol, 1,4-dimethyl-2-naphthol, 3,6-dimethyl-2-naphthol, 3,7-dimethyl-2-naphthol, 6,7-dimethyl-2-naphthol, 1-chloro-2-naphthol, 3-chloro-2-napthol, 4-chloro-2-naphthol, 5-chloro-2-naphthol, 6-chloro-2-naphthol, 7-chloro-2-naphthol, 8-chloro-2-naphthol, 1,3-dichloro-2-naphthol, 1,4-dichloro-2-naphthol, 1-bromo-2-naphthol, 3-bromo-2-naphthol, 4-bromo-2-naphthol, 5-bromo-2-naphthol, 6-bromo-2-naphthol, 7-bromo-2-naphthol, 8-bromo-2-naphthol, 1-methyl-6-bromo-2-naphthol, 1-ethyl-6-bromo-2-naphthol, 1,6-dibromo-2-naphthol, 3,6-dibromo-2-naphthol, 3,7-dibromo-2-naphthol and 4,6-dibromo-2-naphthol.

For the preparation of the novel compounds of formula I, wherein the substituent Z₁ and/or Z₂ signifies a --SO₂ --R₁₂ radical, sulfinates are employed, preferably zinc sulfinates of the formula Zn (SO₂ --R₁₂)₂. They allow the introduction of, for example, the following radicals: methylsulfonyl, chloromethylsulfonyl, ethylsulfonyl, 2-chloroethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec.-butylsulfonyl, n-amylsulfonyl, isoamylsulfonyl, n-hexylsulfonyl, cyclohexylsulfonyl, benzylsulfonyl, phenylsulfonyl, 2,4-dimethylphenylsulfonyl, 4-methylphenylsulfonyl, 4-methoxyphenylsulfonyl, 4-chlorophenylsulfonyl, 4-chloro-3-methylphenylsulfonyl and 4-bromophenylsulfonyl.

The compounds of the present invention are valuable intermediates, in particular for the preparation of dyestuffs, preferably of azo dyestuffs. As far as these azo dyes do not contain ionogenic groups, they may be employed as disperse dyes for dyeing and printing synthetic hydrophobic fiber material, whereas those azo dyes which do contain ionogenic groups are suited for dyeing and printing cotton, wool, silk, polyamide and modified polyacrylonitrile.

Moreover, the compounds of the present invention are valuable pest control agents -- in particular if they are employed as insectizides -- as well as valuable pharmaceuticals, above all if they are employed as analeptics, analgetics and diuretics.

Azo dyes containing the compounds of the present invention may be prepared, for instance, by diazotizing a diazotizable aromatic amine and coupling it with a compound of the present invention. The diazotization and the coupling are carried out in the usual manner. According to the respective initial products employed, this working method leads to the preparation, for instance, of disperse dyes, reactive dyes, cationic dyes or acid dyes. All of these azo dyes exhibit outstanding tinctorial properties, in particular a high coloring strength and a very good fastness to light, perspiration, water, sea water, alkalies and to washing. The disperse dyes distinguish themselves above all by an excellent fastness to dry-heat pleating and setting, ozone, water-gas fading and to rubbing, by a high resistance when subjected to various permanent press treatments and by a good covering power even when applied onto textured polyester materials. The reactive dyes distinguish themselves in particular by an even color depth obtained in the different setting processes. The azo dyes mentioned hereinbefore are suited for dyeing and printing textile materials according to various known processes. The preparation of the dyes as well as their application for dyeing and printing are described in Examples 15 - 19.

In the following examples, "p.b.w." means parts by weight.

EXAMPLE 1

To a composition of 320 p.b.w. ethyl alcohol and 83.7 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine, which are placed in an autoclave, there are added 51.0 p.b.w. liquid ammonia and subsequently the reaction liquid is heated for 18 hours at 200°C. After cooling, the ethyl alcohol is then distilled off, the residue agitated with 300 p.b.w. water, drawn off, washed with water and dried. The resulting 2,6-diamino-3-cyano-4-methylpyridine having the formula ##SPC17##

may be purified by crystallization from ethyl alcohol.

Analysis: C₇ H₈ N₄ -- Calculated: 37.8% N Found: 37.4% N.

EXAMPLE 2

A solution of 400 p.b.w. ethyl alcohol, 93.0 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine and 274.0 p.b.w. diethylamine is agitated 24 hours at 50°C. Upon cooling of the reaction solution, the resulting 2-chloro-3-cyano-4-methyl-6-diethylaminopyridine of the formula ##SPC18##

is crystallized out. The pyridine derivative is then drawn off and washed on the suction apparatus first with 100 p.b.w. ethyl alcohol and subsequently with 500 p.b.w. water. The substance is analytically pure. Its constitution, i.e., the exchange of the 6-position halogen atom in the 2,6-dichloro-3-cyano-4-methylpyridine against the diethylamino group was assured by NMR absorption analysis.

Analysis: C₁₁ H₁₄ ClN₃ -- Calculated: 18.8% N, 15.7% Cl. Found: 18.5%, 15.7% Cl.

EXAMPLE 3

The mixture of Example 2 is agitated in an autoclave for 12 hours at 150°C. Upon cooling, the ethyl alcohol is then distilled off and the residue agitated with 50 p.b.w. water and 245 p.b.w. soda lye, 33° Be. The resulting 2,6-bis-(diethylamino)-3-cyano-4-methylpyridine of the formula ##SPC19##

is an oil which is isolated with ether. It may be purified by vacuum distillation.

Analysis: C₁₅ H₂₄ N₄ -- Calculated: 21.5% N, Found: 21.5% N.

EXAMPLE 4

Introduced into 200 p.b.w. methyl alcohol while cooling were 3.7 p.b.w. sodium. Added to this sodium methyl solution then were 33.5 p.b.w. 2-chloro-3-cyano-4-methyl-6-diethylaminopyridine and subsequently the reaction solution was heated to the point of boiling for 24 hours. Then the methyl alcohol was distilled off, the residue taken up with 100 p.b.w. water, drawn off, washed with water and dried. The resulting 2-methoxy-3-cyano-4-methyl-6-diethylaminopyridine of the formula ##SPC20##

may be purified by recrystallization from methanol.

Analysis: C₁₂ H₁₇ N₃ O -- Calculated: 19.2% N, 14.2% --OCH₃. Found: 19.0% N, 13.8% --OCH₃.

EXAMPLE 5

A composition consisting of 432 p.b.w. n-propylamine and 187 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine is agitated in an autoclave for 2 hours at 100°C. Upon cooling, the reaction liquor is decomposed in water, the resulting 2-chloro-3-cyano-4-methyl-6-n-propylaminopyridine having the formula ##SPC21##

is drawn off and washed with water. It may be purified by recrystallization from ethyl alcohol.

Analysis: C₁₀ H₁₂ ClN₃ -- Calculated: 20.1% N, 16.7% Cl. Found: 20.3% N, 17.0% Cl.

EXAMPLE 6

A composition of 100 p.b.w. 3-dimethylaminopropylamine(1) and 41.8 p.b.w. 2-chloro-3-cyano-4-methyl-6-n-propylaminopyridine are agitated for 2 hours at 140°C. The reaction melt upon cooling is stirred with water, the residue is drawn off and washed with water. The resulting 2-(3'-dimethylamino-n-propylamino)-3-cyano-4-methyl-6-n-propylaminopyridine having the formula ##SPC22##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₅ H₂₅ N₅ -- Calculated: 25.4% N, Found: 25.2% N.

EXAMPLE 7

Introduced into a solution of 155 p.b.w. monomethylamine in 1000 p.b.w. isopropylalcohol are 187 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine. Subsequently, the reaction solution is heated in an autoclave for 5 hours at 200°C. Upon cooling to room temperature, the resulting 2,6-bis-(monomethylamino)-3-cyano-4-methylpyridine having the formula ##SPC23##

is drawn off, first washed with isopropyl alcohol, then with water and dried. It may be purified by crystallization from isopropyl alcohol.

Analysis: C₉ H₁₂ N₄ -- Calculated: 31.8% N, Found: 32.0% N.

EXAMPLE 8

A composition of 200 p.b.w. ethyl alcohol, 83.7 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine and 180 p.b.w. 3-methoxypropylamine-(1) is heated in an autoclave for 18 hours at 180°C. Upon cooling, the ethyl alcohol is distilled off, the residue is stirred with 100 p.b.w. water with the addition of 150 p.b.w. soda lye, 33°Be, drawn off, washed with water and dried. The resulting 2,6-bis-(3'-methoxy-n-propylamino)-3-cyano-4-methylpyridine having the formula ##SPC24##

may be purified by vacuum distillation.

Analysis: C₁₅ H₂₄ N₄ O₂ -- Calculated: 19.2% N, Found: 19.6% N.

EXAMPLE 9

A composition consisting of 100 p.b.w. morpholine and 37.4 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine is heated for 30 minutes at 130°C. The reaction melt is then decomposed on ice the residue is drawn off, washed with water, and dried. The resulting 2,6-bis-(morpholino)-3-cyano-4-methylpyridine having the formula ##SPC25##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₅ H₂₀ N₄ O₂ -- Calculated: 19.4% N, Found: 19.7% N.

EXAMPLE 10

There are introduced 37.2 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine into 150.0 p.b.w. aniline. This reaction solution is then heated for 24 hours at 150°C. and subsequently decomposed in 1,000 p.b.w. ice with the addition of 350 p.b.w. crude hydrochloric acid (D = 1.153). The resulting 2,6-bis-(anilino)-3-cyano-4-methylpyridine having the formula ##SPC26##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₉ H₁₆ N₄ -- Calculated: 18.7% N, Found: 18.5% N

EXAMPLE 11

Introduced into 80 p.b.w. methyl alcohol are 7.6 p.b.w. sodium during cooling, then there are added 27.9 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine to this sodium methylate solution and subsequently the reaction solution is heated to the point of boiling for 24 hours. Then the methyl alcohol is distilled off. The residue is taken up with 100 p.b.w. water, drawn off, washed with water and dried. The resulting 2,6-dimethoxy-3-cyano-4-methylpyridine having the formula ##SPC27##

may be purified by recrystallization from methyl alcohol.

Analysis: C₉ H₁₀ N₂ O₂ -- Calculated: 15.7% N, 34.8% --OCH₃. Found: 15.5% N, 34.2% --OCH₃

EXAMPLE 12

There are introduced 27.9 p.b.w. of 2,6-dichloro-3-cyano-4-methylpyridine into a sodium ethylate solution, which had been prepared from 80 p.b.w. ethyl alcohol and 3.8 p.b.w. sodium. Subsequently, the reaction solution is heated to the point of boiling for 24 hours. The ethyl alcohol is then distilled off, the residue is stirred with 100 p.b.w. water, and the resulting 2-chloro-3-cyano-4-methyl-4-ethoxypyridine having the formula ##SPC28##

is taken up with ether. It may be purified by vacuum distillation.

Analysis: C₉ H₉ ClN₂ O -- Calculated: 14.3% N, 17.8% Cl. Found: 14.5% N, 17.6% Cl.

In the following table there are presented further pyridine compounds prepared in accordance with the herein described process: ##SPC29##

or tautomeric formulae.

    __________________________________________________________________________                                                Empirical                                                                             Cal'd.                                                                             Found                    No.                                                                                 Z.sub.1             Z.sub.2           Formula                                                                               N%  N%                       __________________________________________________________________________     1. --NHCH.sub.2 CH.sub.3                                                                              --NHCH.sub.2 CH.sub.3                                                                              C.sub.11 H.sub.16 N.sub.4                                                             27.5                                                                               27.5                     2. --NHCH.sub.2 CH.sub.2 OH                                                                           --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2                                                                               23.7                                                                               24.0                     3. --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                    --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                    C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2                                                                               21.2                                                                               21.0                     4. --NHCH.sub.2 CH.sub.2 CN                                                                           --NHCH.sub.2 CH.sub.2 CN                                                                           C.sub.13 H.sub.14 N.sub.6                                                             33.1                                                                               33.5                     5. --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                     --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                     C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.6                        CH.sub.3            CH.sub.3                                                6. --NH--CH∠     --NH--CH∠     C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.4                        CH.sub.3            CH.sub.3                                                7. --NH--(CH.sub.2).sub.2 CH.sub.2 OCH.sub.3                                                          --NH--(CH.sub.2).sub.2 CH.sub.2 OCH.sub.                                                           C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2                                                                               19.2                                                                               19.0                     8. --NHCH.sub.2 CH=CH.sub.2                                                                           --NHCH.sub.2 CH=CH.sub.2                                                                           C.sub.13 H.sub.16 N.sub.4                                                             24.6                                                                               24.2                     9. --NH--C.sub.4 H.sub.9 (n)                                                                          --NH--C.sub.4 H.sub.9 (n)                                                                          C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               21.8                     10.                                                                               --NH--C.sub.4 H.sub.9 (sec)                                                                        --NH--C.sub.4 H.sub.9 (sec)                                                                        C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               21.3                        CH.sub.2 --CH.sub.3 CH.sub.2 --CH.sub.3                                     11.                                                                               --NH--CH∠     --NH--CH∠     C.sub.17 H.sub.28 N.sub.4                                                             19.4                                                                               19.8                        CH.sub.2 --CH.sub.3 CH.sub.2 --CH.sub.3                                     12.                                                                               --NH--C.sub.5 H.sub.11 (iso)                                                                       --NH--C.sub.5 H.sub.11 (iso)                                                                       C.sub.17 H.sub.28 N.sub.4                                                             19.4                                                                               19.6                     13.                                                                               --NH--C.sub.6 H.sub.13 (n)                                                                         --NH--C.sub.6 H.sub.13 (n)                                                                         C.sub.19 H.sub.34 N.sub.4                                                             17.7                                                                               18.1                     14.                                        C.sub.19 H.sub.28 N.sub.4                                                             17.9                                                                               17.5                     15.                                        C.sub.21 H.sub.20 N.sub.4                                                             17.1                                                                               17.5                     16.                                        C.sub.23 H.sub.24 N.sub.4                                                             15.7                                                                               15.5                     17.                                        C.sub.27 H.sub.20 N.sub.4                                                             14.0                                                                               14.3                     18.                                                                               HC----CN            HC----CH            C.sub.17 H.sub.16 N.sub.4                                                      O.sub.2                                                                               18.2                                                                               18.5                        ∥∥                                                                               ∥∥                                       HCC--CH.sub.2 --NH--                                                                               HCC--CH.sub.2 --NH--                                       ∠             ∠                                                    O                   O                                                       19.                                        C.sub.19 H.sub.18 N.sub.6                                                             25.5                                                                               25.7                     20.                                                                               H.sub.2 C----CH--NH--                                                                              H.sub.2 C----CH--NH--                                                                              C.sub.15 H.sub.20 N.sub.4                                                      O.sub.4 S.sub.2                                                                       14.6                                                                               15.0                        ||                                                                               ||                                       H.sub.2 CCH.sub.2   H.sub.2 CCH.sub.2                                          ∠             ∠                                                    S                   S                                                          O.sub.2             O.sub.2                                                 21.                                        C.sub.25 H.sub.22 N.sub.6                                                             20.7                                                                               21.0                        CH.sub.3            CH.sub.3                                                22.                                                                               --N∠          --N∠          C.sub.11 H.sub.16 N.sub.4                                                             27.5                                                                               27.2                        CH.sub.3            CH.sub.3                                                   CH.sub.2 CH.sub.2 CN                                                                               CH.sub.2 CH.sub.2 CN                                    23.                                                                               --N∠          --N∠          C.sub.19 H.sub.20 N.sub.8                                                             31.1                                                                               36.7                        CH.sub.2 CH.sub.2 CN                                                                               CH.sub.2 CH.sub.2 CN                                       CH.sub.2 CH.sub.2 CN                                                                               CH.sub.2 CH.sub.2 CN                                    24.                                                                               --N∠          --N∠          C.sub.17 H.sub.22 N.sub.6                                                      O.sub.2                                                                               26.3                                                                               26.8                        CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                       CH.sub.3            CH.sub.3                                                25.                                                                               --N∠          --N∠          C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2                                                                               21.2                                                                               21.6                        CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                       C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n)                                     26.                                                                               --N∠          --N∠          C.sub.19 H.sub.32 N.sub.4                                                      O.sub.2                                                                               16.1                                                                               16.5                        CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                    27.                                                                               --N                 --N                 C.sub.23 H.sub.36 N.sub.4                                                      O.sub.2                                                                               14.0                                                                               14.6                        |          |                                                 CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                    28.                                                                               --N∠          --N∠                                                 CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                                                               C.sub.25 H.sub.28 N.sub.4                                                      O.sub.2                                                                               13.5                                                                               13.2                        C.sub.3 H.sub.7 (n) C.sub.3 H.sub.7 (n)                                     29.                                                                               --N∠          --N∠          C.sub.19 H.sub.32 N.sub.4                                                             17.7                                                                               18.2                        C.sub.3 H.sub.7 (n) C.sub.3 H.sub.7 (n)                                        C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n)                                     30.                                                                               --N∠          --N∠          C.sub.23 H.sub.40 N.sub.4                                                             15.1                                                                               15.5                        C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n)                                        C.sub.6 H.sub.13 (n)                                                                               C.sub.6 H.sub.13 (n)                                    31.                                                                               --N∠          --N∠          C.sub.31 H.sub.56 N.sub.4                                                             11.6                                                                               11.2                        C.sub.6 H.sub.13 (n)                                                                               C.sub.6 H.sub.13 (n)                                    32.                                        C.sub.15 H.sub.20 N.sub.4                                                      O.sub.2                                                                               19.4                                                                               19.6                     33.                                        C.sub.17 H.sub.24 N.sub.4                                                             19.7                                                                               19.3                     34.                                        C.sub.17 H.sub.26 N.sub.6                                                             26.8                                                                               26.2                     35.                                        C.sub.19 H.sub.20 N.sub.6                                                             24.6                                                                               25.1                     36.                                        C.sub.15 H.sub.20 N.sub.4                                                             21.8                                                                               22.2                        CH.sub.3            CH.sub.3                                                37.                                                                               --NH--N|   --NH--N|   C.sub.21 H.sub.22 N.sub.6                                                             23.5                                                                               23.8                        CH.sub.3            CH.sub.3                                                38.                                                                               --NH--N∠      --NH--N∠      C.sub.11 H.sub.18 N.sub.6                                                             35.9                                                                               35.6                        CH.sub.3            CH.sub.3                                                   CH.sub.3 CH.sub.3   CH.sub.3 CH.sub.3                                       39.                                                                               --N----N∠     --N----N∠     C.sub.13 H.sub.22 N.sub.6                                                             32.1                                                                               32.5                        CH.sub.3            CH.sub.3                                                   C.sub.2 H.sub.5      C.sub.2 H.sub.5                                        40.                                                                               --NH--N∠      --NH--N∠      C.sub.15 H.sub.26 N.sub.6                                                             29.0                                                                               22.4                        C.sub.2 H.sub.5     C.sub.2 H.sub.5                                            C.sub.2 H.sub.5     C.sub.2 H.sub.5                                         41.                                                                               --NH--N|   --NH--N|   C.sub.23 H.sub.                                                                       21.8.sub.6                                                                         21.5                     42.                                        C.sub.15 H.sub.22 N.sub.6                                                      O.sub.2                                                                               26.4                                                                               26.2                        CH.sub.3            C.sub.2 H.sub.5                                         43.                                                                               --NHCH.sub.2 CH.sub.2 N∠                                                                     --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.17 H.sub.30 N.sub.6                                                             26.4                                                                               26.0                        CH.sub.3            C.sub.2 H.sub.5                                            C.sub.2 H.sub.5     C.sub.2 H.sub.5                                         44.                                                                               --NHCH.sub.2 CH.sub.2 N∠                                                                     --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.19 H.sub.34 N.sub.6                                                             24.3                                                                               24.5                        C.sub.2 H.sub.5                                                                CH.sub.3            CH.sub.3                                                45.                                                                               --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.17 H.sub.30 N.sub.6                                                             26.4                                                                               26.1                        CH.sub.3            CH.sub.3                                                46.                                        C.sub.21 H.sub.34 N.sub.6                                                      O.sub.2                                                                               20.9                                                                               20.7                     47.                                        C.sub.23 H.sub.38 N.sub.6                                                             21.1                                                                               21.5                     48.                                                                               --NH--OH            --NH--OH            C.sub.7 H.sub.8 N.sub.4                                                        O.sub.2                                                                               31.1                                                                               31.6                        CH.sub.3             CH.sub.3                                               49.                                                                               --N∠          --N∠          C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2                                                                               23.7                                                                               24.2                        OCH.sub.3           OCH.sub.3                                                  CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                    50.                                                                               --N∠          --N∠          C.sub.13 H.sub.20 N.sub.4                                                      O.sub.4                                                                               18.9                                                                               19.3                        OCH.sub.3           OCH.sub.3                                                  CH.sub.2            CH.sub.2                                                51.                                                                               --N∠          --N∠          C.sub.23 H.sub.24 N.sub.4                                                      O.sub.2                                                                               14.4                                                                               15.0                        OCH.sub.3           OCH.sub.3                                                  CH.sub.2 --CH.sub.3 CH.sub.2 --CH.sub.3                                     52.                                                                               --N∠          --N∠          C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2                                                                               19.2                                                                               19.6                        O--CH.sub.2 --CH.sub.3                                                                             O--CH.sub.2 --CH.sub.3                                     CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                    53.                                                                               --N∠          --N∠          C.sub.15 H.sub.24 N.sub.4                                                      O.sub.6                                                                               15.7                                                                               16.2                        O--CH.sub.2 CH.sub.2 OH                                                                            O--CH.sub.2 CH.sub.2 OH                                    CH.sub.2 CH.sub.2 OH                                                                               CH.sub.2 CH.sub.2 OH                                    54.                                                                               --N∠          --N∠          C.sub.25 H.sub.28 N.sub.4                                                      O.sub.4                                                                               12.5                                                                               12.2                        O--CH.sub.2         O--CH.sub.2                                             55.                                                                               H.sub.2 C----CH.sub.2                                                                              H.sub.2 C----CH.sub.2                                                                              C.sub.13 H.sub.16 N.sub.4                                                      O.sub.2                                                                               21.5                                                                               21.2                        ||                                                                               ||                                       --NCH.sub.2         --N∠CH.sub.2                                         ∠             ∠                                                    O                   O                                                          H.sub.2             H.sub.2                                                    C                   C                                                          ∠             ∠-56.         H.sub.2 CCH.sub.2                                                                     H.sub.2 CCH.sub.2                                                                  C.sub.15 H.sub.20                                                              N.sub.4 O.sub.2                                                                    19.4 19.8               ||                                                                               ||                                       --NCH.sub.2         --N∠CH.sub.2                                         ∠             ∠                                                    O                   O                                                       57.                                                                               --NH.sub.2          --Cl                C.sub.7 H.sub.6 ClN.sub.3                                                             25.1                                                                               25.4                     58.                                                                               --NH.sub.2          --CN                C.sub.8 H.sub.6 N.sub.4                                                               35.7                                                                               35.5                     59.                                                                               --NH.sub.2          --OH                C.sub.7 H.sub.7 N.sub.3                                                               28.2                                                                               28.6                     60.                                                                               --NH                --OCH.sub.3         C.sub.8 H.sub.9 N.sub.3                                                               25.8                                                                               25.2                     61.                                                                               -- NH.sub.2                             C.sub.13 H.sub.11 N.sub.3                                                             18.7                                                                               19.1                     62.                                                                               --NH.sub.2          --SH                C.sub.7 H.sub.7 N.sub.3                                                               25.5                                                                               25.7                     63.                                                                               --NH.sub.2          --SC.sub.2 H.sub.5  C.sub.9 H.sub.11 N.sub.3                                                              21.8                                                                               22.3                     64.                                                                               --NH.sub.2          --SO.sub.2 --CH.sub.3                                                                              C.sub.8 H.sub.9 N.sub.3                                                        O.sub.2 S                                                                             19.9                                                                               20.5                     65.                                                                               --NH.sub.2          --NH--CH.sub.3      C.sub.8 H.sub.10 N.sub.4                                                              34.6                                                                               34.2                     66.                                                                               --NH.sub.2          --NH--C.sub.2 H.sub.5                                                                              C.sub.9 H.sub.12 N.sub.4                                                              31.8                                                                               31.5                     67.                                                                               --NH.sub.2          --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.11 H.sub.16 N.sub.4                                                             25.5                                                                               25.2                     68.                                                                               --NH.sub.2                              C.sub.13 H.sub.12 N.sub.4                                                             25.0                                                                               25.5                     69.                                                                               --NH.sub.2                              C.sub.14 H.sub.14 N.sub.4                                                             23.6                                                                               24.1                     70.                                                                               --NH.sub.2                              C.sub.16 H.sub.14 N.sub.5                                                             25.4                                                                               25.0                                            CH.sub.3                                                71.                                                                               --NH.sub.2          --N∠          C.sub.9 H.sub.12 N.sub.4                                                              31.8                                                                               31.6                                            CH.sub.3                                                                       CH.sub.3                                                72.                                                                               --NH.sub.2          --N∠          C.sub.10 H.sub.14 ON.sub.4                                                            27.2                                                                               27.7                                            CH.sub.2 CH.sub.2 OH                                                           CH.sub.2 CH.sub.2 OH                                    73.                                                                               --NH.sub.2          --N∠          C.sub.11 H.sub.16 O.sub.2                                                      N.sub.4                                                                               23.7                                                                               24.2                                            CH.sub.2 CH.sub.2 OH                                    74.                                                                               --NH.sub.2                              C.sub.11 H.sub.14 ON.sub.4                                                            25.7                                                                               26.2                     75.                                                                               --NH.sub.2                              C.sub.12 H.sub.16 N.sub.4                                                             25.9                                                                               26.3                                            CH.sub.3                                                76.                                                                               --NH.sub.2          --NH--N∠      C.sub.9 H.sub.13 N.sub.5                                                              36.6                                                                               36.1                                            CH.sub.3                                                                       C.sub.2 H.sub.5                                         77.                                                                               --NH.sub.2          --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.13 H.sub.21 N.sub.5                                                             28.3                                                                               28.1                                            C.sub.2 H.sub.5                                                                CH.sub.2                                                78.                                                                               --NH.sub.2          --NHCH.sub.2 CH.sub.2 N∠|                                                           C.sub.11 H.sub.15 N.sub.5                                                             32.3                                                                               32.2                                            CH.sub.2                                                                       CH.sub.3                                                79.                                                                               --NH.sub.2          --N∠          C.sub.9 H.sub.12                                                                      29.2ub.4                                                                           29.0                                            OCH.sub.3                                                                      C.sub.3 H.sub.7 (iso)                                   80.                                                                               --NH.sub.2          --N∠          C.sub.12 H.sub.18 ON.sub.4                                                            23.9                                                                               23.3                                            O--C.sub.2 H.sub.5                                      81.                                                                               --NH--CH.sub.3      --Cl                C.sub.8 H.sub.8 N.sub.3                                                               23.2                                                                               23.5                     82.                                                                               --NH--CH.sub.3      --CN                C.sub.9 H.sub.8 N.sub.4                                                               32.6                                                                               32.2                     83.                                                                               --NH--CH.sub.3      --OH                C.sub.8 H.sub.9 ON.sub.3                                                              25.8                                                                               26.2                     84 --NH--CH.sub.3      --OC.sub.2 H.sub.5  C.sub.10 H.sub.13 ON.sub.3                                                            22.0                                                                               22.5                     85.                                                                               --NH--CH.sub.3      --SO.sub.2 --C.sub.2 H.sub.5                                                                       C.sub.10 H.sub.13 N.sub.3                                                      O.sub.2 S                                                                             17.6                                                                               17.5                     86.                                                                               --NH--CH.sub.3      --NH--C.sub.3 H.sub.7 (n)                                                                          C.sub.11 H.sub.16 N.sub.4                                                             27.5                                                                               27.1                     87.                                                                               --NH--CH.sub.3      --NH--C.sub.5 H.sub.11 (iso)                                                                       C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               23.5                     88.                                                                               --NH--CH.sub.3                          C.sub.14 H.sub.20 N.sub.4                                                             23.0                                                                               22.5                     89.                                                                               --NH--CH.sub.3                          C.sub.15 H.sub.16 N.sub.4                                                             22.2                                                                               22.0                     90.                                                                               --NH--CH.sub.3                          C.sub.18 H.sub.16 N.sub.4                                                             19.4                                                                               19.0                     91.                                                                               --NH--CH.sub.3      HC------CH          C.sub.13 H.sub.15 N.sub.4                                                             23.0                                                                               22.5                                            ∥∥                                                           HCCH--CH.sub.2 --NH--                                                          ∠                                                                        O                                                                              C.sub.2 H.sub.5                                         92.                                                                               --NH--CH.sub.3      --N∠          C.sub.12 H.sub.18 N.sub.4                                                             25.7                                                                               26.1                                            C.sub.2 H.sub.5                                                                CH.sub.2 CH.sub.2 CN                                    93.                                                                               --NH--CH.sub.3      --N ∠         C.sub.13 H.sub.17 N.sub.5                                                             27.0                                                                               26.5                                            CH.sub.2 CH.sub.2 OH                                    94.                                                                               --NH--CH.sub.3                          C.sub.12 H.sub.16 N.sub.4                                                             25.9                                                                               26.4                     95.                                                                               --NH--CH.sub.3                          C.sub.13 H.sub.19 N.sub.5                                                             28.6                                                                               28.2                                            C.sub.2 H.sub.5                                         96.                                                                               --NH--CH.sub.3      --NH--N∠      C.sub.12 H.sub.19 N.sub.5                                                             30.0                                                                               30.6                                            C.sub.2 H.sub.5                                                                CH.sub.3                                                97.                                                                               --NH--CH.sub.3      --NHCH.sub.2 CH.sub.2 --N∠                                                                   C.sub.12 H.sub.19 N.sub.5                                                             30.0                                                                               30.3                                            CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                    98.                                                                               --NH--CH.sub.3      --N∠          C.sub.12 H.sub.18 N.sub.4                                                      O.sub.2                                                                               22.4                                                                               22.0                                            O--C.sub.2 H.sub.5                                      99.                                                                               --NH--C.sub.2 H.sub.5                                                                              --Cl                C.sub.9 H.sub.10 ClN.sub.3                                                            21.5                                                                               21.3                     100.                                                                              --NH--C.sub.2 H.sub.5                                                                              --CN                C.sub.10 H.sub.10 N.sub.4                                                             30.1                                                                               30.5                     101.                                                                              --NH--C.sub.2 H.sub.5                                                                              --OH                C.sub.9 H.sub.11 N.sub.3                                                              23.7                                                                               23.2                     102.                                                                              --NH--C.sub.2 H.sub.5                                                                              --OC.sub.3 H.sub.7 (n)                                                                             C.sub.12 H.sub.17 N.sub.3                                                             19.2                                                                               19.0                     103.                                                                              --NH--C.sub.2 H.sub.5                                                                              --SCH.sub.3         C.sub.10 H.sub.13 N.sub.3                                                             20.3                                                                               20.7                     104.                                                                              --NH--C.sub.2 H.sub.5                                                                              --SO.sub.2 --C.sub.3 H.sub.7 (n)                                                                   C.sub.12 H.sub.17 N.sub.3                                                      O.sub.2 S                                                                             15.7                                                                               15.5                     105.                                                                              --NH--C.sub.2 H.sub.5                                                                              --NH--CH.sub.3      C.sub.10 H.sub.14 N.sub.4                                                             29.5                                                                               29.0                     106.                                                                              -- NH--C.sub.2 H.sub.5                                                                             --NH--CH.sub.2 --CH.sub.2 --OCH.sub.3                                                              C.sub.12 H.sub.18 N.sub.4                                                             23.9                                                                               23.3                     107.                                                                              --NH--C.sub.2 H.sub.5                                                                              --NH--C.sub.6 H.sub.13 (n)                                                                         C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               21.0                                            CH.sub.3                                                108.                                                                              --NH--C.sub.2 H.sub.5                                                                              --N∠          C.sub.11 H.sub.16 N.sub.4                                                             27.5                                                                               27.3                                            CH.sub.3                                                109.                                                                              --NH--C.sub.2 H.sub.5                   C.sub.14 H.sub.20 N.sub.4                                                             23.0                                                                               22.5                                            CH.sub.3                                                110.                                                                              --NH--C.sub.2 H.sub.5                                                                              --NH--N∠      C.sub.11 H.sub.17 N.sub.5                                                             32.0                                                                               31.6                                            CH.sub.3                                                                       s,153 C.sub.2 H.sub.5                                   111.                                                                              --NH--C.sub.2 H.sub.5                                                                              --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.15 H.sub.25 N.sub.5                                                             25.5                                                                               26.0                                            C.sub.2 H.sub.5                                                                CH.sub.2                                                112.                                                                              --NH--C.sub.2 H.sub.5                                                                              --N∠          C.sub.23 H.sub.24 N.sub.4                                                             15.1                                                                               15.5                                            O--CH.sub.2                                             113.                                                                              --NH-- C.sub.3 H.sub.7 (n)                                                                         --OH                C.sub.10 H.sub.13 N.sub.3                                                             22.0                                                                               22.4                     114.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --O--C.sub.3 H.sub.7 (iso)                                                                         C.sub.13 H.sub.19 N.sub.3                                                             18.0                                                                               18.5                     115.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --SO.sub.2 --C.sub.5 H.sub.11 (iso)                                                                C.sub.15 H.sub.23 N.sub.3                                                      O.sub.2 S                                                                             13.6                                                                               13.3                     116.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --NH--CH.sub.3      C.sub.11 H.sub.16 N.sub.4                                                             27.5                                                                               28.0                     117.                                                                              --NH--C.sub.3; H.sub.7 (n)                                                                         --NH--C.sub.3 H.sub.7 (iso)                                                                        C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.5                     118.                                                                              --NH--C.sub.3 H.sub.7 (n)               C.sub.16 H.sub.24 N.sub.4                                                             20.6                                                                               21.0                     119.                                                                              --NH--C.sub.3 H.sub.7 (n)               C.sub.16 H.sub.18 N.sub.4                                                             21.1                                                                               21.5                                            CH.sub.3                                                120.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --N∠          C.sub.12 H.sub.18 N.sub.4                                                             25.7                                                                               26.0                                            CH.sub.3                                                                       CH.sub.2                                                121.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --N∠          C.sub.19 H.sub.24 N.sub.4                                                             17.3                                                                               17.5                                            CH.sub.2 --CH.sub.2 --OH                                122.                                                                              --NH--C.sub.3 H.sub.7 (n)               C.sub.14 H.sub.21 N.sub.5                                                             25.5                                                                               26.1                                            CH.sub.3                                                123.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.14 H.sub.23 N.sub.5                                                             26.8                                                                               26.4                                            CH.sub.3                                                                       CH.sub.3                                                124.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                          --N∠          C.sub.12 H.sub.18 N.sub.4                                                             23.9                                                                               23.2                                            OCH.sub.3                                               125.                                                                              --NH--C.sub.3 H.sub.7 (iso)                                                                        --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.14 H.sub.22 N.sub.4                                                             21.4                                                                               21.0                                            C.sub.2 H.sub.5                                         126.                                                                              --NH--C.sub.3 H.sub.7 (iso)                                                                        --N∠          C.sub.14 H.sub.22 N.sub.4                                                             22.8                                                                               23.0                                            C.sub.2 H.sub.5                                         127.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                          --Cl                C.sub.11 H.sub.14 ClN.sub.3                                                           18.8                                                                               19.0                     128.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                          --OH                C.sub.11 H.sub.15 N.sub.3                                                             20.5                                                                               21.0                     129.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                          --O--C.sub.4 H.sub.9 (n)                                                                           C.sub.15 H.sub.23 N.sub.3                                                             16.1                                                                               16.4                     130.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                          --NH--CH.sub.3      C.sub.12 H.sub.18 N.sub.4                                                             25.7                                                                               25.0                     131.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                          --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.13 H.sub.20 N.sub.4                                                             22.6                                                                               23.0                                            CH.sub.3                                                132.                                                                              --NH--C.sub.4 H.sub.9 (iso)                                                                        --N∠          C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               23.8                                            CH.sub.3                                                133.                                                                              --NH--C.sub.4 H.sub.9 (iso)             C.sub.16 H.sub.25 N.sub.5                                                             24.4                                                                               24.1                                            C.sub.2 H.sub.5                                         134.                                                                              --NH--C.sub.4 H.sub.9 (sek)                                                                        --N∠          C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               22.0                                            C.sub.2 H.sub.5                                                                CH.sub.3                                                135.                                                                              --NH--C.sub.4 H.sub.9 (sek)                                                                        --NH--N∠      C.sub.13 H.sub.21 N.sub.5                                                             28.3                                                                               28.5                                            CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                    136.                                                                              --NH--C.sub.4 H.sub.9 (sek)                                                                        --N∠          C.sub.16 H.sub.26 N.sub.4                                                      O.sub.2                                                                               18.3                                                                               18.7                                            O--CH.sub.2 CH.sub.2 CH.sub.3                           137.                                                                              --NH--C.sub.4 H.sub.9 (tert)                                                                       --NH--C.sub.2 H.sub.5                                                                              C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.5                     138.                                                                              --NH--C.sub.4 H.sub.9 (tert)                                                                       --NH--CH.sub.2 --CH.sub.2 --CN                                                                     C.sub.14 H.sub.19 N.sub.5                                                             27.2                                                                               27.5                     139.                                                                              --NH--C.sub.5 H.sub.11 (n)                                                                         --NH--CH.sub.3      C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.5                                            CH.sub.3                                                140.                                                                              --NH--C.sub.5 H.sub.11 (n)                                                                         --N∠          C.sub.14 H.sub.22 N.sub.4                                                             22.8                                                                               23.0                                            CH.sub.3                                                141.                                                                              --NH--C.sub.5 H.sub.11 (n)              C.sub.18 H.sub.23 N.sub.5                                                             22.7                                                                               23.2                                            CH.sub.3                                                142.                                                                              --NH--C.sub.5 H.sub.11 (iso)                                                                       --NH--N∠      C.sub.14 H.sub.23 N.sub.5                                                             26.8                                                                               27.2                                            CH.sub.3                                                                       C.sub.2 H.sub.5                                         143.                                                                              --NH--C.sub.6 H.sub.13 (n)                                                                         --N∠          C.sub.17 H.sub.28 N.sub.4                                                             19.4                                                                               19.0                                            C.sub.2 H.sub.5                                         144.                                                                              --NH--C.sub.6 H.sub.13 (n)              C.sub.12 H.sub.26 N.sub.4                                                             18.5                                                                               18.9                                            CH.sub.3                                                145.                                                                              --NH--C.sub.6 H.sub.13 (n)                                                                         --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.17 H.sub.29 N.sub.5                                                             23.1                                                                               23.3                                                                CH.sub.3                            146.                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                           --NH--CH.sub.3      C.sub.10 H.sub.14 N.sub.4                                                             27.2                                                                               27.5                     147.                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                           --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.13 H.sub.20 N.sub.4                                                      O.sub. 2                                                                              21.2                                                                               21.5                                            CH.sub.3                                                148.                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                           --N∠          C.sub.11 H.sub.16 N.sub.4                                                             25.5                                                                               26.0                                            CH.sub.3                                                149.                                                                              --NHCH.sub.2 CH.sub.2 OH                C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2                                                                               21.4                                                                               21.7                     150.                                                                              --NHCH.sub.2 CH.sub.2 OH                C.sub.14 H.sub.20 N.sub.4                                                             21.5                                                                               21.8                                            CH.sub.2                                                151.                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                           --NHCH.sub.2 CH.sub.2 N∠|                                                           C.sub.13 H.sub.19 N.sub.5                                                             26.8                                                                               27.2                                            CH.sub.2                                                152.                                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                    --NH--CH.sub.3      C.sub.11 H.sub.16 N.sub.4                                                             25.5                                                                               25.8                                            CH.sub.3                                                153.                                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.2                                                                    --N∠          C.sub.12 H.sub.18 N.sub.4                                                             23.9                                                                               24.3                                            CH.sub.3                                                                       C.sub.2 H.sub.5                                         154.                   --N∠          C.sub.19 H.sub.24 N.sub.4                                                             17.3                                                                               17.5                                            C.sub.2 H.sub.5                                         155.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                  --NH--C.sub.2 H.sub.5                                                                              C.sub.13 H.sub.17 N.sub.5                                                             28.8                                                                               28.2                                            CH.sub.3                                                156.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                  --N∠          C.sub.14 H.sub.19 N.sub.5                                                             25.6                                                                               26.0                                            CH.sub.2 CH.sub.2 OH                                                           C.sub.2 H.sub.5                                         157.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                  --N∠          C.sub.15 H.sub.21 N.sub.5                                                             25.8                                                                               26.3                                            C.sub.2 H.sub.5                                                                CH.sub.3                                                158.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                  --NH--N|   C.sub.18 H.sub.20 N.sub.6                                                             26.2                                                                               27.0                     159.                                       C.sub.27 H.sub.20 N.sub.4                                                             14.0                                                                               13.5                     160.                                                                              --NH--C.sub.2 H.sub.5                   C.sub.15 H.sub.22 N.sub.4                                                             21.7                                                                               22.2                     161.                                                                              --NH--C.sub.2 H.sub.5                   C.sub.17 H.sub.20 N.sub.4                                                             20.0                                                                               20.4                     162.                                                                              --NH--C.sub.2 H.sub.5                   C.sub.16 H.sub.18 N.sub.4                                                             21.1                                                                               21.5                     163.                                                                              --NH--C.sub.4 H.sub.9 (n)               C.sub.18 H.sub.22 N.sub.4                                                             18.1                                                                               18.6                     164.                                       C.sub.20 H.sub.21 N.sub.5                                                             21.1                                                                               21.7                     165.                                                                              "                   --NH.sub.2          C.sub.13 H.sub.18 N.sub.4                                                             24.3                                                                               24.5                     166.                                                                              "                   --NH--CH.sub.3      C.sub.14 H.sub.20 N.sub.4                                                             23.0                                                                               23.5                     167.                   --NH--CH.sub.2 --CH=CH.sub.2                                                                       C.sub.16 H.sub.22 N.sub.4                                                             20.7                                                                               21.0                     168.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.17 H.sub.26 N.sub.4                                                             19.2                                                                               19.5                                            CH.sub.3                                                169.                                                                              "                   --N∠          C.sub.15 H.sub.22 N.sub.4                                                             21.7                                                                               22.2                                            CH.sub.3                                                170.                                                                              "                                       C.sub.18 H.sub.28 N.sub.6                                                             25.6                                                                               26.0                     171.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.19 H.sub.29 N.sub.5                                                             22.2                                                                               22.5                                            CH.sub.3                                                                       H.sub.2                                                                        C                                                                              ∠                                                 172.                   H.sub.2 CCH.sub.2   C.sub.17 H.sub.24 N.sub.4                                                             18.7                                                                               19.1                                            ||                                                           --NCH.sub.2                                                                    ∠                                                 173.                   --NH.sub.2          C.sub.14 H.sub.14 N.sub.4                                                             23.5                                                                               24.0                     174.                                                                              "                   --NH--C.sub.2 H.sub.5                                                                              C.sub.16 H.sub.18 N.sub.4                                                             21.2                                                                               22.0                                            C.sub.2 H.sub.5                                         175.                                                                              "                   --N∠          C.sub.18 H.sub.22 N.sub.4                                                             19.0                                                                               19.3                                            C.sub.2 H.sub.5                                         176.                                                                              "                   --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                    C.sub.17 H.sub.20 N.sub.4                                                             18.9                                                                               18.4                                            C.sub.2 H.sub.5                                         177.                                                                              "                   --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.20 H.sub.27 N.sub.5                                                             20.8                                                                               21.4                                            C.sub.2 H.sub.5                                         178.                                       C.sub.21 H.sub.21 N.sub.5                                                             20.4                                                                               20.6                                            CH.sub.2                                                179.                   --N∠          C.sub.22 H.sub.22 N.sub.4                                                             15.6                                                                               16.0                                            OCH.sub.3                                               180.                   --NH--CH.sub.3      C.sub.18 H.sub.18 N.sub.4                                                             21.1                                                                               21.5                                            CH.sub.3                                                181.                                                                              "                   --N∠          C.sub.17 H.sub.20                                                                     20.0b.4                                                                            20.5                                            CH.sub.3                                                182.                                                                              "                                       C.sub.17 H.sub.23 N.sub.4                                                             18.7                                                                               19.0                     183.                   --NH.sub.2          C.sub.13 H.sub.12 N.sub.4                                                             25.0                                                                               24.7                     184.                                                                              "                   --NH--CH.sub.3      C.sub.14 H.sub.14 N.sub.4                                                             23.6                                                                               24.2                     185.                                                                              "                   --NH--C.sub.3 H.sub.7 (n)                                                                          C.sub.16 H.sub.18 N.sub.4                                                             21.1                                                                               21.3                     186.                                                                              "                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.15 H.sub.16 N.sub.4                                                             20.9                                                                               21.5                                            CH.sub.3                                                187.                   --N∠          C.sub.15 H.sub.16 N.sub.4                                                             22.2                                                                               22.0                                            CH.sub.3                                                                       CH.sub.2 CH.sub.2 CN                                    188.                                                                              "                   --N∠          C.sub.19 H.sub.18 N.sub.6                                                             25.5                                                                               25.9                                            CH.sub.2 CH.sub.2 CN                                    189.                                       C.sub.17 H.sub.18 N.sub.4                                                             19.1                                                                               19.7                                            C.sub.2 H.sub.5                                         190.                                                                              "                   --NH--N∠      C.sub.17 H.sub.21 N.sub.5                                                             23.7                                                                               24.3                                            C.sub.2 H.sub.5                                                                CH.sub.3                                                191.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.18 H.sub.23 N.sub.5                                                             22.7                                                                               22.3                                            CH.sub.3                                                                       CH.sub.3                                                192.                                                                              "                   --N∠          C.sub.15 H.sub.16 N.sub.4                                                             20.9                                                                               21.4                                            O--CH.sub.3                                             193.                   --NH--CH.sub.3      C.sub.14 H.sub.13 ClN.sub.4                                                           20.6                                                                               20.2                     194.                   --NH--CH.sub.3      C.sub.15 H.sub.16 N.sub.4                                                             22.2                                                                               22.8                                            CH.sub.3                                                195.                   --N∠          C.sub.17 H.sub.20 N.sub.4                                                             20.0                                                                               20.5                                            CH.sub.3                                                196.                   "                   C.sub.16 H.sub.18 N.sub.4                                                             19.9                                                                               20.3                     197.                                                                              HC------ CH         --NH--CH.sub.3      C.sub.13 H.sub.14 N.sub.4                                                             23.1                                                                               23.5                        ∥∥                                                           --NH--CH.sub.2 --CCH                                                           ∠                                                                        O                                                                                                  CH.sub.3                                                198.                                                                              "                   --N∠          C.sub.14 H.sub.16 N.sub.4                                                             21.9                                                                               21.5                                            CH.sub.3                                                                       C.sub.2 H.sub.5                                         199.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.19 H.sub.27 N.sub.5                                                             20.5                                                                               20.9                                            C.sub.2 H.sub.5                                         200.                   --NH--CH.sub.3      C.sub.14 H.sub.15 N.sub.5                                                             27.7                                                                               27.2                     201.                   --NH--CH.sub.3      C.sub.14 H.sub.15 N.sub.5                                                             27.7                                                                               28.2                     202.                   --NH--CH.sub.3      C.sub.15 H.sub.17 N.sub.5                                                             26.2                                                                               26.0                     203.                   --NH--CH.sub.3      C.sub.15 H.sub.17 N.sub.5                                                             26.2                                                                               26.6                     204.                                                                              --NH--HC----CH.sub.2                                                                               --NH--CH.sub.3      C.sub.12 H.sub.16 N.sub.4                                                      O.sub.2 S                                                                             20.0                                                                               20.5                        ||                                                           H.sub.2 CCH.sub.2                                                              ∠                                                                        S                                                                              O.sub.2                                                                                            CH.sub.3                                                205.                                                                              "                   --N∠          C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                             19.0                                                                               18.7                                            CH.sub.3                                                206.                                                                              "                                       C.sub.15 H.sub.20 N.sub.4                                                      O.sub.3 S                                                                             16.7                                                                               17.1                                            CH.sub.3                                                207.                                                                              "                   --NH--N∠      C.sub.13 H.sub.19 N.sub.5                                                      O.sub.2 S                                                                             22.7                                                                               22.2                                            CH.sub.3                                                208.                   --NH--CH.sub.3      C.sub.17 H.sub.17 N.sub.5                                                             24.1                                                                               24.5                                            CH.sub.3                                                209.                                                                              "                   --N∠          C.sub.18 H.sub.19 N.sub.5                                                             23.0                                                                               23.5                                            CH.sub.3                                                210.                                                                              "                                       C.sub.20 H.sub.21 N.sub.5                                                             20.2                                                                               20.5                     211.                   --Cl                C.sub.13 H.sub.16 ClN.sub.3                                                           16.9                                                                               16.5                     212.                                                                              "                   --OH                C.sub.13 H.sub.17 N.sub.3                                                             18.2                                                                               18.6                     213.                                                                              "                   --OCH.sub.3         C.sub.14 H.sub.19 N.sub.3                                                             17.1                                                                               17.6                     214.                                                                              "                   --CN                C.sub.14 H.sub.16 N.sub.4                                                             25.0                                                                               25.3                     215.                                                                              "                                       C.sub.20 H.sub.23 N.sub.3                                                      O.sub.2 S                                                                             11.4                                                                               11.2                     216.                   --Cl                C.sub.14 H.sub.12 ClN.sub.3                                                           16.3                                                                               16.0                     217.                                                                              "                   --OH                C.sub.14 H.sub.13 N.sub.3                                                             17.6                                                                               18.0                     218.                                                                              "                   --O--CH.sub.3       C.sub.15 H.sub. 15 N.sub.3                                                            16.6                                                                               16.0                     219.                                                                              "                   --S--C.sub.4 H.sub.9 (n)                                                                           C.sub.18 H.sub.21 N.sub.3                                                             21.5                                                                               21.8                     220.                   --Cl                C.sub.13 H.sub.10 ClN.sub.3                                                           17.3                                                                               17.0                     221.                   --CN                C.sub.14 H.sub.10 N.sub.4                                                             23.9                                                                               24.3                     222.                                                                              "                   --OH                C.sub.13 H.sub.11 N.sub.3                                                             18.7                                                                               18.5                     223.                                                                              "                   --OCH.sub.3         C.sub.14 H.sub.13 N.sub.3                                                             17.6                                                                               17.3                     224.                                                                              "                   --SCH.sub.3         C.sub.14 H.sub.13 N.sub.3                                                             16.5                                                                               16.0                        CH.sub.3                                                                    225.                                                                              --N∠          --Cl                C.sub.9 H.sub.10 ClN.sub.3                                                            21.5                                                                               21.0                        CH.sub.3                                                                    226.                                                                              "                   --CN                C.sub.10 H.sub.10 N.sub.4                                                             30.1                                                                               30.5                     227.                                                                              "                   --OH                C.sub.9 H.sub.11 N.sub.3                                                              23.7                                                                               23.4                     228.                                                                              "                   --OCH.sub.3         C.sub.10 H.sub.13 N.sub.3                                                             22.0                                                                               22.3                     229.                                                                              "                   --SO.sub.2 --C.sub.2 H.sub.5                                                                       C.sub.11 H.sub.15 N.sub.3                                                      O.sub.2 S                                                                             16.6.                                                                              17.0                     230.                                                                              "                   --NH--CH.sub.3      C.sub.10 H.sub.14 N.sub.4                                                             29.5                                                                               29.1                     231.                                                                              "                   --NH--C.sub.3 H.sub.7 (n)                                                                          C.sub.12 H.sub.18 N.sub.4                                                             25.7                                                                               26.2                     232.                                                                              "                   --NH--C.sub.6 H.sub.13 (n)                                                                         C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               21.8                        CH.sub.3                                                                    233.                                                                              --N∠                              C.sub.15 H.sub.22 N.sub.4                                                             21.7                                                                               21.5                        CH.sub.3                                                                    234.                                                                              "                                       C.sub.16 H.sub.18 N.sub.4                                                             21.1                                                                               20.7                     235.                                                                              "                                       C.sub.15 H.sub.16 N.sub.4                                                             22.2                                                                               22.6                     236.                                                                              "                                       C.sub.19 H.sub.18 N.sub.4                                                             18.5                                                                               18.9                     237.                                                                              "                   HC------CH          C.sub.14 H.sub.16 N.sub.4                                                             21.9                                                                               21.5                                            ∥∥                                                           HCC--CH.sub.2 --NH--                                                           ∠                                                                        O                                                                              C.sub.2 H.sub.5                                         238.                                                                              "                   --N∠          C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               23.8                                            C.sub.2 H.sub.5                                            CH.sub.3            CH.sub.2 CH.sub.2 CN                                    239.                                                                              -- N∠         --N∠          C.sub.14 H.sub.19 N.sub.5                                                             25.6                                                                               26.0                        CH.sub.3            CH.sub.2 CH.sub.2 OH                                    240.                                                                              "                                       C.sub.13 H.sub.18 N.sub.4                                                             24.3                                                                               24.5                        CH.sub.3                                                                    241.                                                                              --N∠                              C.sub.14 H.sub.21 N.sub.5                                                             27.0                                                                               27.4                        CH.sub.3                                                                                           C.sub.2 H.sub.5                                         242.                                                                              "                   --NH--N∠      C.sub.13 H.sub.21 N.sub.5                                                             28.3                                                                               27.9                                            C.sub.2 H.sub.5                                                                CH.sub.3                                                243.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.14 H.sub.23 N.sub.5                                                             26.8                                                                               26.6                                            CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                    244.                                                                              "                   --N∠          C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2                                                                               21.2                                                                               21.6                                            O--C.sub.2 H.sub.5                                         C.sub.2 H.sub.5                                                             245.                                                                              --N∠          --Cl                C.sub.11 H.sub.14 ClN.sub.3                                                           18.8                                                                               18.5                        C.sub.2 H.sub.5                                                             246.                                                                              "                   --CN                C.sub.12 H.sub.14 N.sub.4                                                             26.2                                                                               26.6                     247.                                                                              "                   --OH                C.sub.11 H.sub.15 N.sub.3                                                             20.5                                                                               21.0                     248.                                                                              "                   --OCH.sub.3         C.sub.12 H.sub.17 N.sub.3                                                             19.2                                                                               19.0                     249.                                                                              "                   --SC.sub.2 H.sub.5  C.sub.13 H.sub.19 N.sub.3                                                             16.8                                                                               17.2                        C.sub.2 H.sub.5                                                             250.                                                                              --N∠          --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                   C.sub.15 H.sub.23 N.sub.3                                                      SO.sub.2                                                                              13.6                                                                               13.5                        C.sub.2 H.sub.5                                                                C.sub.2 H.sub.5                                                             251.                                                                              --N∠          --NH--CH.sub.3      C.sub.12 H.sub.17 N.sub.4                                                             25.7                                                                               25.5                        C.sub.2 H.sub.5                                                             252.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.15 H.sub.24 N.sub.4                                                             20.3                                                                               20.0                     253.                                                                              "                                       C.sub.17 H.sub.25 N.sub.4                                                             19.6                                                                               19.5                     254.                                                                              "                                       C.sub.18 H.sub.22 N.sub.4                                                             19.0                                                                               19.4                     255.                                                                              "                                       C.sub.17 H.sub.20 N.sub.4                                                             20.0                                                                               20.2                     256.                                                                              "                                       C.sub.16 H.sub.24 N.sub.4                                                             20.6                                                                               21.0                                            CH.sub.3                                                257.                                                                              "                   --NH--N∠      C.sub.13 H.sub.21 N.sub.5                                                             28.3                                                                               28.0                                            CH.sub.3                                                                       CH.sub.3                                                258.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            C.sub.16 H.sub.27 N.sub.5                                                             24.2                                                                               24.5                                            CH.sub.3                                                   C.sub.2 H.sub.5     CH.sub.3                                                259.                                                                              --N∠          --N∠          C.sub.13 H.sub.20 N.sub.4                                                             22.6                                                                               22.2                        C.sub.2 H.sub.5     OCH.sub.3                                                  CH.sub.2 CH.sub.2 CN                                                        260.                                                                              --N∠          --OCH.sub.3         C.sub.13 H.sub.16 N.sub.4                                                      O.sub.2                                                                               21.5                                                                               21.3                        CH.sub.2 CH.sub.2 OH                                                        261.                                                                              "                                       C.sub.16 H.sub.21 N.sub.5                                                      O.sub.2                                                                               22.2                                                                               22.6                        CH.sub.2 CH.sub.2 OH                                                        262.                                                                              --N∠          --NH.sub.2          C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2                                                                               23.7                                                                               23.4                        CH.sub.2 CH.sub.2 OH                                                           CH.sub.2 CH.sub.2 OH                                                                               CH.sub.3                                                263.                                                                              --N∠          --N∠          C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2                                                                               21.2                                                                               21.5                         CH.sub.2 CH.sub.2 OH                                                                              CH.sub.3                                                264.                                                                              "                                       C.sub.17 H.sub.20 N.sub.4                                                      O.sub.2                                                                               17.9                                                                               18.2                        CH.sub.2 CH.sub.2 CN                                                        265.                                                                              --N∠          --OCH.sub.3         C.sub.14 H.sub.15 N.sub.5                                                             26.0                                                                               26.3                        CH.sub.2 CH.sub.2 CN                                                                               CH.sub.3                                                266.                                                                              "                   --N∠          C.sub.15 H.sub.18 N.sub.6                                                             29.8                                                                               29.5                                            CH.sub.3                                                   CH.sub.3                                                                    267.                                                                              --N∠          --NH.sub.2          C.sub.10 H.sub.14 N.sub.4                                                             27.2                                                                               27.5                        CH.sub.2 CH.sub.2 OH                                                        268.                                                                              "                   --NH--CH.sub.3      C.sub.11 H.sub.16 N.sub.4                                                             25.5                                                                               25.8                     269.                                                                              "                                       C.sub.16 H.sub.24 N.sub.5                                                             23.2                                                                               23.7                     270.                                                                              "                                       C.sub.16 H.sub.18 N.sub.4                                                             19.9                                                                               19.5                                            CH.sub.3                                                271.                                                                              "                   --NH--N∠      C.sub.12 H.sub.19 N.sub.5                                                             28.1                                                                               27.8                                            CH.sub.3                                                   C.sub.3 H.sub.7 (iso)                                                       272.                                                                              --N∠          --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.16 H.sub.26 N.sub.4                                                      O.sub.2                                                                               13.8                                                                               14.2                        CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n)                                                         273.                                                                              --N∠          --NH--CH.sub.3      C.sub.14 H.sub.22 N.sub.4                                                             21.4                                                                               21.0                        CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n)                                                         274.                                                                              --N∠                              C.sub.17 H.sub.26 N.sub.4                                                      O.sub.2                                                                               17.6                                                                               18.0                        CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n) CH.sub.3                                                275.                                                                              --N∠          --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.17 H.sub.29 N.sub.5                                                             21.9                                                                               21.7                        CH.sub.2 CH.sub.2 OH                                                                               CH.sub.3                                                276.                                                                              --N                 --NH--CH.sub.3      C.sub.16 H.sub.23 N.sub.4                                                             19.4                                                                               19.0                        |                                                                     CH.sub.2 CH.sub.2 OH                                                        277.                                                                              --N                                     C.sub.21 H.sub.32 N.sub.4                                                             15.7                                                                               16.3                        |                                                                     CH.sub.2 CH.sub.2 OH                                                        278.                                                                              --N                 --NH.sub.2          C.sub.16 H.sub.18 N.sub.4                                                             19.9                                                                               19.5                        |                                                                     CH.sub.2 CH.sub.2 OH                                                        279.                                                                              --N                 --NH--CH.sub.3      C.sub.17 H.sub.20 N.sub.4                                                             18.9                                                                               19.5                        |                                                                     CH.sub.2 CH.sub.2 OH                                                        280.                                                                              "                                       C.sub.23 H.sub.25 N.sub.5                                                             18.1                                                                               18.5                        C.sub.3 H.sub.7 (n)                                                         281.                                                                              --N∠          --Cl                C.sub.13 H.sub.18 ClN.sub.3                                                           16.7                                                                               16.5                        C.sub.3 H.sub.7 (n)                                                         282.                                                                              "                   --NH.sub.2          C.sub.13 H.sub.20 N.sub.4                                                             24.1                                                                               24.5                     283.                                                                              "                   --CN                C.sub.14 H.sub.18 N.sub.4                                                             23.1                                                                               23.7                        C.sub.3 H.sub.7 (n)                                                         284.                                                                              --N∠          --OH                C.sub.13 H.sub.19 N.sub.3                                                             18.0                                                                               18.4                        C.sub.3 H.sub.7 (n)                                                         285.                                                                              "                   --OCH.sub.3         C.sub.14 H.sub.21 N.sub.3                                                             17.0                                                                               17.5                     286.                                                                              "                   --SO.sub.2 --CH.sub.3                                                                              C.sub.14 H.sub.21 N.sub.3                                                      O.sub.2 S                                                                             14.2                                                                               13.8                     287.                                                                              "                   --NH--CH.sub.3      C.sub.14 H.sub.22 N.sub.4                                                             22.8                                                                               23.2                     288.                                                                              "                   --NH--C.sub.3 H.sub.7 (n)                                                                          C.sub.16 H.sub.26 N.sub.4                                                             20.5                                                                               21.0                     289.                                                                              "                                       C.sub.19 H.sub.30 N.sub.4                                                             17.8                                                                               17.5                     290.                                                                              "                                       C.sub.19 H.sub.24 N.sub.4                                                             18.2                                                                               18.5                                            CH.sub.3                                                291.                                                                              "                   --N∠          C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               20.8                                            CH.sub.3                                                292.                                                                              "                                       C.sub.17 H.sub.27 N.sub.5                                                             22.1                                                                               22.5                        C.sub.3 H.sub.7 (n) CH.sub.3                                                293.                                                                              --N∠          --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.17 H.sub.29 N.sub.5                                                             23.1                                                                               23.6                        C.sub.3 H.sub.7 (n) CH.sub.3                                                                       CH.sub.3                                                294.                                                                              "                   --N∠          C.sub.15 H.sub.23 N.sub.4                                                             20.3                                                                               20.0                                            OCH.sub.3                                                  C.sub.3 H.sub.7 (iso)                                                       295.                                                                              --N∠          --NH.sub.2          C.sub.13 H.sub.20 N.sub.4                                                             24.2                                                                               24.6                        C.sub.3 H.sub.7 (iso)                                                       296.                                                                              "                   --OH                C.sub.13 H.sub.19 N.sub.3                                                             18.0                                                                               18.5                        C.sub.3 H.sub.7 (iso)                                                       297.                                                                              --N∠          --NH--CH.sub.3      C.sub.14 H.sub.22 N.sub.4                                                             22.8                                                                               22.5                        C.sub.3 H.sub.7 (iso)                                                       298.                                                                              "                                       C.sub.18 H.sub.28 N.sub.4                                                             18.7                                                                               19.1                        C.sub.4 H.sub.9 (n) --Cl                C.sub.15 H.sub.22 ClN.sub.3                                                           15.0                                                                               15.4                        C.sub.4 H.sub.9 (n)                                                         300.                                                                              "                   --CN                C.sub.16 H.sub.22 N.sub.4                                                             20.7                                                                               21.0                        C.sub.4 H.sub.9 (n)                                                         301.                                                                              --N∠          --OH                C.sub.15 H.sub.23 N.sub.3                                                             16.1                                                                               16.5                        C.sub.4 H.sub.9 (n)                                                         302.                                                                              "                   --OCH.sub.3         C.sub.16 H.sub.25 N.sub.3                                                             15.3                                                                               15.0                     303.                                                                              "                   --NH--CH.sub.3      C.sub.16 H.sub.26 N.sub.4                                                             20.4                                                                               20.8                     304.                                                                              "                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.17 H.sub.28 N.sub.4                                                             18.4                                                                               18.1                     305.                                                                              "                                       C.sub.21 H.sub.34 N.sub.4                                                             16.4                                                                               16.8                     306.                                                                               "                                      C.sub.19 H.sub.30 N.sub.4                                                             17.0                                                                               17.3                                            CH.sub.3                                                307.                                                                              "                   --NH--N∠      C.sub.17 H.sub.29 N.sub.5                                                             23.1                                                                               23.5                                            CH.sub.3                                                308.                                                                              "                                       C.sub.19 H.sub.31 N.sub.5                                                             20.3                                                                               21.0                        C.sub.4 H.sub.9 (iso)                                                       309.                                                                              --N∠          --NH.sub.2          C.sub.15 H.sub.24 N.sub.4                                                             21.5                                                                               21.9                        C.sub.4 H.sub.9 (iso)                                                       310.                                                                              "                   --NH--CH.sub.3      C.sub.16 H.sub.26 N.sub.4                                                             20.4                                                                               20.6                        C.sub.4 H.sub.9 (iso)                                                       311.                                                                              --N∠          --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.17 H.sub.28 N.sub.4                                                             18.4                                                                               18.5                        C.sub.4 H.sub.9 (iso)                                                          C.sub.4 H.sub.9 (iso)                                                                              CH.sub.3                                                312.                                                                              --N∠          --NHCH.sub.2 CH.sub.2 N∠                                                                     C.sub.19 H.sub.33 N.sub.5                                                             21.1                                                                               21.5                        C.sub.4 H.sub.9 (iso)                                                                              CH.sub.3                                                   C.sub.5 H.sub.11 (n)                                                        313.                                                                              --N∠          --NH.sub.2          C.sub.17 H.sub.28 N.sub.4                                                             19.4                                                                               20.0                        C.sub. 5 H.sub.11 (n)                                                       314.                                                                              "                   --NH--CH.sub.3      C.sub.18 H.sub.30 N.sub.4                                                             18.5                                                                               18.2                     315.                                                                              "                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.19 H.sub.32 N.sub.4                                                             16.9                                                                               17.5                        C.sub.6 H.sub.13 (n)                                                        316.                                                                              --N∠          --NH.sub.2          C.sub.19 H.sub.32 N.sub.4                                                             17.7                                                                               18.0                        C.sub.6 H.sub.13 (n)                                                        317.                                                                              "                   --NH--CH.sub.3      C.sub.20 H.sub.34 N.sub.4                                                             17.0                                                                               16.7                     318.                                                                              "                                       C.sub.25 H.sub.36 N.sub.4                                                             14.3                                                                               14.7                     319.                   --NH.sub.2          C.sub.11 H.sub.14 N.sub.4                                                             25.7                                                                               26.2                     320.                                                                              "                   --OH                C.sub.11 H.sub.13 N.sub.3                                                      O.sub.2                                                                               19.2                                                                               19.5                     321.                                                                              "                   --NH--CH.sub.3      C.sub.12 H.sub.16 N.sub.4                                                             24.1                                                                               24.5                                            C.sub.2 H.sub.5                                         322.                   --N∠          C.sub.15 H.sub.22 N.sub.4                                                             20.4                                                                               21.0                                            C.sub.2 H.sub.5                                         323.                   --NH.sub.2          C.sub.11 H.sub.14 N.sub.4                                                             27.7                                                                               28.0                     324.                                                                              "                   --NH--CH.sub.3      C.sub.12 H.sub.16 N.sub.4                                                             25.9                                                                               25.7                                            CH.sub.3                                                325.                                                                              "                   --N∠          C.sub.13 H.sub.18 N.sub.4                                                             24.3                                                                               25.0                                            CH.sub.3                                                326.                   --OH                C.sub.12 H.sub.15 N.sub.3                                                             19.3                                                                               19.5                     327.                                                                              "                   --NH.sub.2          C.sub.12 H.sub.16 N.sub.4                                                             25.9                                                                               25.5                     328.                                                                              "                   --NH--CH.sub.3      C.sub.13 H.sub.18 N.sub.4                                                             24.3                                                                               24.7                     329.                                                                              "                   --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.16 H.sub.24 N.sub.4                                                             19.4                                                                               19.5                                            CH.sub.3                                                330.                                                                              "                   --N∠          C.sub.14 H.sub.20 N.sub.4                                                             22.9                                                                               23.0                                            CH.sub.3                                                331.                                                                              "                                       C.sub.18 H.sub.26 N.sub.4                                                             18.8                                                                               18.5                     332.                                       C.sub.18 H.sub.20 N.sub.4                                                             19.2                                                                               19.2                     333.                   --NH.sub.2          C.sub.12 H.sub.17 N.sub.5                                                             30.4                                                                               30.6                     334.                                                                              "                   --NH--CH.sub.3      C.sub.13 H.sub.19 N.sub.5                                                             28.5                                                                               28.7                                            CH.sub. 3                                               335.                                                                              "                   --N∠          C.sub.14 H.sub.21 N.sub.5                                                             27.0                                                                               27.5                                            CH.sub.3                                                336.                   --NH--CH.sub.3      C.sub.14 H.sub.21 N.sub.5                                                             27.0                                                                               27.3                        CH.sub.3 CH.sub.3                                                           337.                                                                              --N----N∠     --NH--CH.sub.3      C.sub.11 H.sub.17 N.sub.5                                                             32.0                                                                               32.3                        CH.sub.3                                                                    338.                                                                              "                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.12 H.sub.19 N.sub.5                                                             28.1                                                                               28.0                        CH.sub.3                                                                    339.                                                                              --NH--N∠      --NH.sub.2          C.sub.9 H.sub.13 N.sub.5                                                              36.7                                                                               37.0                        CH.sub.3                                                                    340.                                                                              "                   --NH--CH.sub.3      C.sub.10 H.sub.15 N.sub.5                                                             34.1                                                                               34.5                        C.sub.2 H.sub.5     CH.sub.3                                                341.                                                                              --NH--N∠      --N∠          C.sub.13 H.sub.21 N.sub.5                                                             28.4                                                                               29.0                        C.sub.2 H.sub.5     CH.sub.3                                                                       CH.sub.3                                                342.                                                                              "                   --N∠          C.sub.14 H.sub.23 N.sub.5                                                             25.3                                                                               25.5                                            CH.sub.2 CH.sub.2 OH                                    343.                                                                              "                                       C.sub.17 H.sub.                                                                       23.8.sub.5                                                                         24.0                        CH.sub.3                                                                    344.                                                                              --NH--N|   --NH--CH.sub.3      C.sub.15 H.sub.17 N.sub.5                                                             26.2                                                                               26.6                                            CH.sub.3                                                345.                                                                              "                   --N∠          C.sub.16 H.sub.19 N.sub.5                                                             24.9                                                                               25.5                                            CH.sub.3                                                346.                   --NH--CH.sub.3      C.sub.13 H.sub.17 N.sub.5                                                             28.9                                                                               29.0                                            CH.sub.3                                                347.                                                                              "                   --N∠          C.sub.14 H.sub.19 N.sub.5                                                             27.3                                                                               27.5                                            CH.sub.3                                                348.                   --NH.sub.2          C.sub.12 H.sub.17 N.sub.5                                                             30.3                                                                               31.6                     349.                                                                              "                   --NH--CH.sub.3      C.sub.13 H.sub.19 N.sub.5                                                             28.6                                                                               29.0                                            CH.sub.3                                                350.                                                                              "                   --N∠          C.sub.14 H.sub.21 N.sub.5                                                             27.1                                                                               26.8                                            CH.sub.3                                                351.                   --NH--CH.sub.3      C.sub.12 H.sub.17 N.sub.5                                                             28.4                                                                               28.6                                            CH.sub.3                                                352.                                                                              "                   --N∠          C.sub.13 H.sub.19 N.sub.5                                                             26.8                                                                               27.0                                            CH.sub.3                                                   CH.sub.3                                                                    353.                                                                              --NHCH.sub.2 CH.sub.2 N∠                                                                     --NH--CH.sub.3      C.sub.12 H.sub.19 N.sub.5                                                             30.1                                                                               29.5                        CH.sub.3                                                                       C.sub.2 H.sub.5                                                             354.                                                                              --NHCH.sub.2 CH.sub.2 N∠                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.15 H.sub.25 N.sub.5                                                             24.1                                                                               24.6                        C.sub.2 H.sub.5                                                                CH.sub.3                                                                    355.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            --NH--CH.sub.3      C.sub.13 H.sub.21 N.sub.5                                                             28.4                                                                               29.0                        CH.sub.3                                                                    356.                                                                              "                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.14 H.sub.23 N.sub.5                                                             25.3                                                                               25.5                        C.sub.2 H.sub.5                                                             357.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                            --NH--CH.sub.3      C.sub.15 H.sub.25 N.sub.5                                                             25.5                                                                               26.0                        C.sub.2 H.sub.5                                                             358.                   --NH--CH.sub.3      C.sub.15 H.sub.23 N.sub.5                                                             24.1                                                                               23.7                     359.                   --NH--CH.sub.3      C.sub.16 H.sub.25 N.sub.5                                                             24.3                                                                               25.0                     360.                   --NH--CH.sub.3      C.sub.15 H.sub.23 N.sub.5                                                             25.7                                                                               26.0                     361.                   --NH--CH.sub.3      C.sub.16 H.sub.26 N.sub.6                                                             27.8                                                                               27.5                     362.                                                                              --NH--OH            --NH--CH.sub.3      C.sub.8 H.sub.10 N.sub.4                                                              31.5                                                                               31.9                        CH.sub.3                                                                    363.                                                                              --N∠          --NH--CH.sub.3      C.sub.10 H.sub.14 N.sub.4                                                             27.2                                                                               27.7                        OCH.sub.3                                                                      CH.sub.2 CH.sub.2 OH                                                        364.                                                                              --N∠          --NH--CH.sub.3      C.sub.11 H.sub.16 N.sub.4                                                             25.5                                                                               25.1                        OCH.sub.3                                                                   365.                                                                              --N                 --NH--CH.sub.3      C.sub.16 H.sub.18 N.sub.4                                                             19.8                                                                               19.2                        |                                                                     OCH.sub.3                                                                      CH.sub.3                                                                    366.                                                                              CH∠           --NH--CH.sub.3      C.sub.13 H.sub.20 N.sub.4                                                             22.6                                                                               23.0                        CH.sub.3                                                                       --N∠                                                                     OCH.sub.2 CH.sub.3                                                             H.sub.2 CCH.sub.2                                                              ||                                                        367.                                                                              --NCH.sub.2         --NH--CH.sub.3      C.sub.11 H.sub.14 N.sub.4                                                             25.6                                                                               25.6                        ||                                                           O                                                                              H.sub.2 C-- --CH.sub.2                                                      368.                                                                              --N∠∠CH.sub.2                                                                          --NH--CH.sub.3      C.sub.12 H.sub.16 N.sub.4                                                             24.1                                                                               24.5                        O----CH.sub.2                                                               369.                                                                              --CN                --Cl                C.sub.8 H.sub.4 ClN.sub.3                                                             23.7                                                                               24.2                     370.                                                                              --CN                --CN                C.sub.9 H.sub.4 N.sub.4                                                               33.3                                                                               33.8                     371.                                                                              --CN                --OH                C.sub.8 H.sub.5 N.sub.3                                                               26.4                                                                               27.0                     372.                                                                              --CN                --OCH.sub.3         C.sub.9 H.sub.7 N.sub.3                                                               24.3                                                                               24.0                     373.                                                                              --CN                --NH.sub.2          C.sub.8 H.sub.6 N.sub.4                                                               35.4                                                                               35.8                     374.                                                                              --CN                --NH--CH.sub.3      C.sub.9 H.sub.8 N.sub.4                                                               32.6                                                                               33.0                                            CH.sub.3                                                375.                                                                              --CN                --N∠          C.sub.10 H.sub.10 N.sub.4                                                             30.1                                                                               30.5                                            CH.sub.3                                                                       CH.sub.3                                                376.                                                                              --CN                --N∠          C.sub.11 H.sub.12 N.sub.4                                                             25.9                                                                               26.4                                            CH.sub.2 CH.sub.2 OH                                    377.                                                                              --CN                                    C.sub.13 H.sub.14 N.sub.4                                                             24.8                                                                               25.2                                            CH.sub.3                                                378.                                                                              --CN                --NH--N∠      C.sub.10 H.sub.11                                                                     34.8b.5                                                                            35.2                                            CH.sub.3                                                379.                                                                              --CN                --NH--OCH.sub.3     C.sub.9 H.sub.8 N.sub.4                                                               29.8                                                                               29.5                     380.                                                                              --OCH.sub.3         --Cl                C.sub.8 H.sub.7 ClN.sub.2                                                             15.4                                                                               15.0                     381.                                                                              --OC.sub.2 H.sub.5  --Cl                C.sub.9 H.sub.9 ClN.sub.2                                                             14.3                                                                               14.7                     382.                                                                              --OC.sub.4 H.sub.9 (n)                                                                             --Cl                C.sub.11 H.sub.13 ClN.sub.2                                                           12.5                                                                               12.8                     383.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                     --Cl                C.sub.10 H.sub.11 ClN.sub.2                                                           12.4                                                                               12.0                     384.                                                                              --OCH.sub.3         --OCH.sub.3         C.sub.9 H.sub.10 N.sub.2                                                       O.sub.2                                                                               15.7                                                                               16.0                     385.                                                                              --OCH.sub.3         --OC.sub.2 H.sub.5  C.sub.10 H.sub.12 N.sub.2                                                      O.sub.2                                                                               14.6                                                                               14.8                     386.                                                                              --OC.sub.2 H.sub.5  --OC.sub.2 H.sub.5  C.sub.11 H.sub.14 N.sub.2                                                      O.sub.2                                                                               13.6                                                                               13.9                     387.                                                                              --OCH.sub.3         --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                     C.sub.11 H.sub.14 N.sub.2                                                      O.sub.3                                                                               12.6                                                                               12.2                     388.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                     --OCH.sub.3         C.sub.11 H.sub.14 N.sub.2                                                      O.sub.3                                                                               12.6                                                                               13.0                     389.                                                                              --OCH.sub.3                             C.sub.14 H.sub.12 N.sub.2                                                      O.sub.2                                                                               11.7                                                                               11.9                     390.                                                                              --OCH.sub.3         --SC.sub.4 H.sub.9 (n)                                                                             C.sub.12 H.sub.16 N.sub.2                                                             11.9                                                                               12.1                     391.                                                                              --OC.sub.2 H.sub.5  --SC.sub.2 H.sub.5  C.sub.11 H.sub.16 N.sub.2                                                             12.6                                                                               13.0                     392.                                                                              --OCH.sub.3                             C.sub.14 H.sub.12 N.sub.2                                                             10.9                                                                               12.1                     393.                                                                              --OCH.sub.3                             C.sub.15 H.sub.14 N.sub.2                                                      O.sub.2                                                                               11.0                                                                               11.5                     394.                                                                              --OCH.sub.3         --NH--CH.sub.3      C.sub.9 H.sub.11 N.sub.3                                                              23.7                                                                               23.5                     395.                                                                              --OCH.sub.3         --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.10 H.sub.13 N.sub.3                                                      O.sub.2                                                                               20.8                                                                               21.2                     396.                                                                              --OC.sub.2 H.sub.5  --NH--(CH.sub.2).sub.3 --OCH.sub.3                                                                 C.sub.13 H.sub.19 N.sub.3                                                      O.sub.2                                                                               16.9                                                                               17.3                     397.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3          C.sub.16 H.sub.17 N.sub.3                                                      O.sub.2                                                                               14.8                                                                               15.0                                            CH.sub.3                                                398.                                                                              --OC.sub.4 H.sub.9 (n)                                                                             --NH--(CH.sub.2).sub.3 --N∠                                                                  C.sub.16 H.sub.26 N.sub.4                                                             19.3                                                                               19.5                                            CH.sub.3                                                                       CH.sub.3                                                399.                                                                              --OCH.sub.3         --N∠          C.sub.11 H.sub.15 N.sub.3                                                      O.sub.2                                                                               19.0                                                                               19.3                                            CH.sub.2 CH.sub.2 OH                                    400.                                                                              --OC.sub.2 H.sub.5                      C.sub.13 H.sub.16 N.sub.3                                                      O.sub.2                                                                               17.1                                                                               17.5                     401.                                                                              --SCH.sub.3         --Cl                C.sub.8 H.sub.7 CIN.sub.2                                                             14.1                                                                               14.5                     402.                                                                              --SC.sub.2 H.sub.5  --Cl                C.sub.9 H.sub.9 ClN.sub.2                                                             13.2                                                                               13.0                     403.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --Cl                C.sub.11 H.sub.13 ClN.sub.2                                                           11.7                                                                               12.1                     404.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --OCH.sub.3         C.sub.12 H.sub.16 N.sub.2                                                             11.9                                                                               12.3                     405.                                                                              --SC.sub.2 H.sub.5                      C.sub.15 H.sub.14 N.sub.2                                                             10.4                                                                               11.0                     406.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --SC.sub.4 H.sub.9 (n)                                                                             C.sub.15 H.sub.22 N.sub.2                                                      S.sub.2                                                                               9.5 10.0                     407.                                                                              --SCH.sub.3         --NH--CH.sub.3      C.sub.9 H.sub.11 N.sub.3                                                              21.7                                                                               22.0                     408.                                                                              --SC.sub.2 H.sub.5  --NH--(CH.sub.2).sub.3 .sub.[OCH.sub.3                                                             C.sub.13 H.sub.19 N.sub.3                                                             15.8                                                                               16.0                     409.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.13 H.sub.19 N.sub.3                                                             15.8                                                                               16.2                     410.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --NH                C.sub.17 H.sub.19 N.sub.3                                                             14.1                                                                               14.5                                            CH.sub.3                                                411.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --NH--(CH.sub.2).sub.3 --N∠                                                                  C.sub.16 H.sub.26 N.sub.4                                                             18.3                                                                               18.5                                            CH.sub.3                                                                       CH.sub.3                                                412.                                                                              --SC.sub.4 H.sub.9 (n)                                                                             --N∠          C.sub.14 H.sub.21 N.sub.3                                                             15.0                                                                               15.5                                            CH.sub.2 CH.sub.2 OH                                    413.                                                                              --SC.sub.4 H.sub.9 (n)                  C.sub.15 H.sub.21 N.sub.3                                                             14.4                                                                               15.0                     414.                                                                              --SO.sub.2 --CH.sub.3                                                                              --Cl                C.sub.10 H.sub.10 ClN.sub.3                                                    O.sub.2 S                                                                             15.5                                                                               15.0                     415.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                   --Cl                C.sub.13 H.sub.16 ClN.sub.3                                                    O.sub.2 S                                                                             13.4                                                                               13.8                     416.                   --Cl                C.sub.15 H.sub.12 ClN.sub.3                                                    O.sub.2 S                                                                             12.6                                                                               12.5                     417.                                                                              --SO.sub.2 --CH.sub.3                                                                              --CN                C.sub.11 H.sub.10 N.sub.4                                                      O.sub.2 S                                                                             21.4                                                                               21.0                     418.                                                                              --SO.sub.2 --CH.sub.3                                                                              --OH                C.sub.10 H.sub.11 N.sub.3                                                      O.sub.3 S                                                                             16.6                                                                               17.2                     419.                                                                              --SO.sub.2 --CH.sub.3                                                                              --OCH.sub.3         C.sub.11 H.sub.13 N.sub.3                                                      O.sub.3 S                                                                             15.7                                                                               15.3                     420.                                                                              --SO.sub.2 --CH.sub.3                                                                              --SCH.sub.3         C.sub.11 H.sub.13 N.sub.3                                                      O.sub.2 S.sub.2                                                                       14.8                                                                               15.4                     421.                                                                              --SO.sub.2 --CH.sub.3                                                                              --SO.sub.2 --CH.sub.3                                                                              C.sub.11 H.sub.13 N.sub.3                                                      O.sub.4 S.sub.2                                                                       13.3                                                                               12.9                     422.                                                                              --SO.sub.2 --CH.sub.3                                                                              --NH.sub.2          C.sub.10 H.sub.12 N.sub.4                                                      O.sub.2 S                                                                             22.2                                                                               22.6                                            CH.sub.3                                                423.                                                                              --SO.sub.2 --C.sub.2 H.sub.5                                                                       --N∠          C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                             19.1                                                                               18.5                                            CH.sub.3                                                424.                                                                              --SO.sub.2 --CH.sub.3                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.13 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                             18.1                                                                               18.7                                            CH.sub.3                                                425.                                                                              --SO.sub.2 --CH.sub.3                                                                              --N∠          C.sub.13 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                             18.1                                                                               18.3                                            CH.sub.3                                                426.                                                                              --SO.sub.2 --CH.sub.3                   C.sub.14 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                             17.4                                                                               17.6                                            CH.sub.3                                                427.                                                                              --SO.sub.2 --C.sub.2 H.sub.5                                                                       --NH--(CH.sub.2).sub.2 --N∠                                                                  C.sub.15 H.sub.23 N.sub.5                                                      O.sub.2 S                                                                             20.8                                                                               20.1                                            CH.sub.3                                                428.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                   --NHCH.sub.2 CH.sub.2 OH                                                                           C.sub.15 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                             17.4                                                                               17.8                     429.                   --NH--CH.sub.3      C.sub.17 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                             16.4                                                                               16.0                     430.                   --NH--CH.sub.3      C.sub.16 H.sub.16 N.sub.4                                                      O.sub.2 S                                                                             17.1                                                                               17.8                     431.                                       C.sub.33 H.sub.25 N.sub.7                                                             18.9                                                                               18.5                     432.                   --Cl                C.sub.23 H.sub.20 ClN.sub.5                                                           17.5                                                                               17.9                     433.                   --OCH.sub.3         C.sub.24 H.sub.23 N.sub.5                                                             17.6                                                                               17.0                                            CH.sub.3                                                434.                   --N∠          C.sub.25 H.sub.26 N.sub.6                                                             20.5                                                                               21.2                                            CH.sub.3                                                435.                                                                              "                                       C.sub.37 H.sub.33 N.sub.7                                                             17.0                                                                               17.2                     436.                                       C.sub.39 H.sub.37 N.sub.7                                                             16.3                                                                               16.6                     437.                   --OCH.sub.3         C.sub.26 H.sub.28 N.sub.6                                                             19.1                                                                               19.8                     438.                                                                              "                   --NH--CH.sub.3      C.sub.26 H.sub.29 N.sub.7                                                             22.3                                                                               22.5                     439.                                                                              "                                       C.sub.41 H.sub.43 N.sub.9                                                             19.1                                                                               19.8                     440.                                       C.sub.33 H.sub.25 N.sub.7                                                             18.9                                                                               18.1                     441.                   --Cl                C.sub.21 H.sub.15 ClN.sub.4                                                           15.0                                                                               15.4                     442.                                                                              "                   --OC.sub.2 H.sub.5  C.sub.23 H.sub.20 N.sub.4                                                      O.sub.2                                                                               14.5                                                                               15.0                     443.                                                                              "                                       C.sub.33 H.sub.23 N.sub.5                                                      O.sub.2                                                                               13.4                                                                               13.7                     444.                                       C.sub.33 H.sub.23 N.sub.5                                                      S.sub.2                                                                               12.7                                                                               12.5                     __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the process of this invention: ##SPC30##

or tautomeric forms.

    __________________________________________________________________________                                                Empirical Cal'd.                                                                              Found                No.  Y           Z.sub.1       Z.sub.2     Formula   N%   N%                   __________________________________________________________________________     445.                                                                               --H          --NH.sub.2    --Cl        C.sub.6 H.sub.7 N.sub.2                                                                  20.1 20.7                 446.                                                                               --H          --NH.sub.2    --NH.sub.2  C.sub.6 H.sub.9 N.sub.3                                                                  34.1 33.6                 447.                                                                               --H          --NH.sub.2    --OH        C.sub.6 H.sub.8 N.sub.2                                                                  22.6 22.8                 448.                                                                               --H          --NH.sub.2    --OCH.sub.3 C.sub.7 H.sub.10 N.sub.2                                                                 20.3 20.1                 449.                                                                               --H          --NH.sub.2    --SC.sub.2 H.sub.5                                                                         C.sub.8 H.sub.12 N.sub.2                                                                 16.6 17.1                 450.                                                                               --H          --NH.sub.2    --SO.sub.2 --CH.sub.3                                                                      C.sub.7 H.sub.10 N.sub.2                                                       O.sub.2 S 15.0 15.2                 451.                                                                               --H          --NH.sub.2    --NH--CH.sub.3                                                                             C.sub.7 H.sub.11 N.sub.3                                                                 30.6 31.0                 452.                                                                               --H          --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.8 H.sub.13 N.sub.3                                                                 27.8 28.2                 453.                                                                               --H          --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                   C.sub. 10 H.sub.17 N.sub.3                                                     O.sub.2   19.9 20.2                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 454.                                                                               --H          --N∠    --N∠  C.sub.14 H.sub.25 N.sub.3                                                                17.9 17.3                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 455.                                                                               --H                                    C.sub.14 H.sub.21 N.sub.3                                                      O.sub.2   16.0 16.3                                                CH.sub.3                                        456.                                                                               --H          --NHCH.sub.2 CH.sub.2 CH.sub.3                                                               --NHCH.sub.2 CH.sub.2 N∠                                                             C.sub.13 H.sub.23 N.sub.4                                                                23.8 23.2                                                CH.sub.3                                        457.                                                                               --NH.sub.2   --NH.sub.2    --NH.sub.2  C.sub.6 H.sub.10 N.sub.4                                                                 40.6 40.8                 458.                                                                               --NH.sub.2   --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.8 H.sub.14 N.sub.4                                                                 33.7 33.2                                  CH.sub.3      CH.sub.3                                        459.                                                                               --NH.sub.2   --N∠    --N∠  C.sub.10 H.sub.18 N.sub.4                                                                28.9 28.7                                  CH.sub.3      CH.sub.3                                        460.                                                                               --NH.sub.2   --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                   C.sub.10 H.sub.18 N.sub.4                                                      O.sub.2   24.8 25.1                 461.                                                                               --NO         --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.8 H.sub.12 N.sub.4                                                                 31.1 31.0                                  CH.sub.3      CH.sub.3                                        462.                                                                               --NO         --N∠    --N∠  C.sub.10 H.sub.16 N.sub.4                                                                26.9 26.7                                  CH.sub.3      CH.sub.3                                        463.                                                                               --NO                                   C.sub.14 H.sub.20 N.sub.4                                                      O.sub.3   19.2 19.5                 464.                                                                               --NO.sub.2   --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.8 H.sub.12 N.sub.4                                                       O.sub.2   28.5 28.5                                  CH.sub.3      CH.sub.3                                        465.                                                                               --NO.sub.2   --N∠    --N∠  C.sub.10 H.sub.16 N.sub.4                                                      O.sub.2   25.0 25.3                                  CH.sub.3      CH.sub.3                                        466.                                                                               --NO.sub.2                             C.sub.14 H.sub.20 N.sub.4                                                      O.sub.4   18.2 18.5                 467.                                                                               --CH.sub.3   --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.9 H.sub.15 N.sub.3                                                                 25.4 26.0                 468.                                                                               --CH.sub.2 --CH.sub.3                                                                       --NH--CH.sub.3                                                                               --NH--CH.sub.2 --CH.sub.3                                                                  C.sub.11 H.sub.19 N.sub.3                                                                21.7 22.0                 469.                                                                               --CH.sub.2 CH.sub.2 CN                                                                      --NH.sub.2    --NH.sub.2  C.sub.9 H.sub.12 N.sub.4                                                                 31.8 32.0                 470.             --NH.sub.2    --NH.sub.2  C.sub.15 H.sub.17 N.sub.3                                                                16.5 17.0                 471.                                                                               --CH.sub.2 CH.sub.2 N--C.sub.2 H.sub.5                                                      --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.19 H.sub.26 N.sub.4                                                                17.2 17.5                     C.sub.2 H.sub.5                                                            472.                                                                               --CH.sub.2 CH.sub.2 N∠                                                                --NH--CH.sub.3                                                                               --OCH.sub.2 CH.sub.2 =CH.sub.2                                                             C.sub.16 H.sub.27 N.sub.3                                                                15.2 15.3                     C.sub.2 H.sub.5                                                            473.                                                                               --CH.sub.2 --CH=CH.sub.2                                                                    --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.11 H.sub.17 N.sub.3                                                                22.0 22.4                     CH.sub.3                                                                       |                                                                 474.                                                                               --CH.sub.2 --C=CH.sub.2                                                                     --NH--CH.sub.3                                                                               --SO.sub.2 CH.sub.2 CH=CH.sub.2                                                            C.sub.14 H.sub.20 N.sub.2                                                      O.sub.2 S 10.0 9.8                  475.                                                                               --C.sub.3 H.sub.7 (n)                                                                       --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                           C.sub.15 H.sub.27 N.sub.                                                                 16.8 16.5                 476.                                                                               --C.sub.4 H.sub.9 (n)                                                                       --NH--CH.sub.3            C.sub.17 H.sub.28 N.sub.2                                                                10.1 9.7                  477.                                                                               --C.sub.4 H.sub.9 (iso)                                                                     --NH--CH.sub.3            C.sub.18 H.sub.24 N.sub.2                                                                9.9  10.2                 478.                                                                               --C.sub.6 H.sub.13 (n)                                                                      --NH--CH.sub.3            C.sub.18 H.sub.24 N.sub.2                                                                9.9  10.4                 479.             --NH--C.sub.3 H.sub.7 (iso)                                                                  --OCH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.19 H.sub.32 N.sub.2                                                                9.4  9.5                  480.             --NH--CH.sub.3                                                                               --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                    C.sub.19 H.sub.27 N.sub.4                                                                18.0 18.3                                                CH.sub.3                                                                       CH.sub.3                                                                       |                                      481.             --NH.sub.2    --O--CH.sub.2 --C=CH.sub.2                                                                 C.sub.16 H.sub.18 N.sub.2                                                                11.0 10.5                                                CH.sub.3                                        482.             --NH.sub.2    --S--CH∠                                                                             C.sub.16 H.sub.20 N.sub.2                                                                9.7  9.5                                                 CH.sub.3                                        483.             --NH--CH.sub.3            C.sub.20 H.sub.19 ClN.sub.2                                                              7.9  8.3                  484.             --NH--CH.sub.3            C.sub.21 H.sub.20 Cl.sub.2                                                     N.sub.2 S 6.9  6.8                  485.             --NH.sub.2    --NH.sub.2  C.sub.12 H.sub.20 N.sub.4                                                                23.7 23.9                                  CH.sub.3      CH.sub.3                                        486.                                                                               "            --N∠    --N∠  C.sub.16 H.sub.28 N.sub.4                                                                19.2 19.7                                  CH.sub.3      CH.sub.3                                        487.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.15 H.sub.26 N.sub.4                                                                21.4 21.6                 488.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.14 H.sub.24 N.sub.4                                                                22.6 22.2                 489.                                                                               --COOCH.sub.3                                                                               --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.10 H.sub.15 N.sub.3                                                      O.sub.2   20.1 20.3                 490.                                                                               --COOC.sub.2 H.sub.5                                                                        --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.11 H.sub.17 N.sub.3                                                      O.sub.2   18.8 18.5                                  C.sub. 2 H.sub.5                                                                             C.sub.2 H.sub.5                                 491.                                                                               --COOC.sub.2 H.sub.5                                                                        --N∠    --N∠  C.sub.17 H.sub.29 N.sub.3                                                      O.sub.2   13.7 14.0                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 492.                                                                               --COOC.sub.2 H.sub.5       --NH--CH.sub.3                                                                             C.sub.14 H.sub.21 N.sub.3                                                      O.sub.3   15.0 14.8                 493.                                                                               --COOC.sub.4 H.sub.9 (n)                                                                    --NHCH.sub.2 CH.sub.2 OH  C.sub.15 H.sub.25 N.sub.3                                                      O.sub.4   13.5 13.8                                                CH.sub.3                                        494.                                                                               --COOC.sub.6 H.sub.13 (n)                                                                   --NHCH.sub.2 CH.sub.2 CH.sub.3                                                               --NHCH.sub.2 CH.sub.2 N∠                                                             C.sub.20 H.sub.36 N.sub.4                                                      O.sub.2   15.4 15.0                                                CH.sub.3                                        495.                                                                               --COCH.sub.3 --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.10 H.sub.15 N.sub.3                                                                21.7 21.5                 496.                                                                               --CO--CH=CH.sub.2                                                                           --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.11 H.sub.15 N.sub.3                                                                20.5 20.7                                                CH.sub.3                                        497.                                                                               --CO--C.sub.6 H.sub.13 (n)                                                                  --NH--CH.sub.3                                                                               --N∠  C.sub. 16 H.sub.27 N.sub.3                                                               15.2 15.3                                                CH.sub.3                                        498.             --NH--CH.sub.3                                                                               "           C.sub.16 H.sub.25 N.sub.3                                                                15.3 15.5                 499.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.16 H.sub.19 N.sub.3                                                                15.6 15.8                 500.             --NH.sub.2    --NH.sub.2  C.sub.13 H.sub.13 N.sub.3                                                                18.5 18.3                 501.                                                                               "            --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.15 H.sub.17 N.sub.3                                                                16.5 16.7                                  CH.sub.3      CH.sub.3                                        502.                                                                               "            --N∠    --N∠  C.sub.17 H.sub.21 N.sub.3                                                                14.8 14.6                                  CH.sub.3      CH.sub.3                                        503.                                                                               "            --NH--CH.sub.3            C.sub.18 H.sub.21 N.sub.3                                                      O.sub.2   13.5 13.2                 504.                                                                               --CO--NH.sub.2                                                                              --NH.sub.2    --Cl        C.sub.7 H.sub.8 ClN.sub.3                                                                22.6 22.8                 505.                                                                               --CO--NH.sub.2                                                                              --NH.sub.2    --NH.sub.2  C.sub.7 H.sub.10 N.sub.4                                                                 33.8 34.2                 506.                                                                               -- CO--NH.sub.2                                                                             --NH.sub.2    --OH        C.sub.7 H.sub.9 N.sub.3                                                        O.sub.2   25.1 24.7                 507.                                                                               --CO--NH.sub.2                                                                              --NH.sub.2    --OC.sub.2 H.sub.5                                                                         C.sub.9 H.sub.13 N.sub.3                                                       O.sub.2   21.5 22.1                 508.                                                                               --CO--NH.sub.2                                                                              --NH.sub.2    --SC.sub.2 H.sub.5                                                                         C.sub.9 H.sub.13 N.sub.3                                                                 19.9 19.6                 509.                                                                               --CO--NH.sub.2                                                                              --NH.sub.2    --SO.sub.2 C.sub.2 H.sub.5                                                                 C.sub.9 H.sub.13 N.sub.3                                                       O.sub.3 S 17.3 17.5                 510.                                                                               --CO--NH.sub.2                                                                              --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.9 H.sub.14 N.sub.4                                                                 28.9 28.7                 511.                                                                               --CO--NH.sub.2                                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                          C.sub.13 H.sub.22 N.sub.4                                                      O.sub.3   19.9 19.6                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 512.                                                                               --CO--NH.sub.2                                                                              --N∠    --N∠  C.sub.15 H.sub.26 N.sub.4                                                                20.1 20.5                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 513.                                                                               --CO--NH.sub.2                                                                              --NHCH.sub.2 CH.sub.3     C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2   21.2 21.4                                                CH.sub.3                                        514.                                                                               --CO--NH.sub.2                                                                              --NHCH.sub.2 CH.sub.3                                                                        --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                    C.sub.14 H.sub.25 N.sub.5                                                                25.1 25.3                                                CH.sub.3                                        515.                                                                               --CO--NH--CH.sub.3                                                                          --NH.sub.2    --NH.sub.2  C.sub.8 H.sub.12 N.sub.4                                                                 31.1 31.0                 516.                                                                               --CONHCH.sub.2 CH.sub.2 OH                                                                  --NH.sub.2    --S--CH.sub.2 --CH=CH.sub.2                                                                C.sub.12 H.sub.17 N.sub.3                                                      O.sub.3   16.7 17.0                 517.                                                                               --CONHC.sub.4 H.sub.9 (n)                                                                   --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.13 H.sub.22 N.sub.4                                                                22.4 22.1                     CH.sub.2                                                                   518.                                                                               --CO--N∠|                                                                    --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                            C.sub.15 H.sub.24 N.sub.4                                                      O.sub.3   18.2 18.6                     CH.sub.2                                                                       C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 519.                                                                               --CO--N∠                                                                              --N∠    --N∠  C.sub.19 H.sub.34 N.sub.4                                                                16.8 17.1                     C.sub.2 H.sub.5                                                                             C.sub.2 H.sub. 5                                                                             C.sub.2 H.sub.5                                 520.             --NH--CH.sub.3                                                                               --NH--C.sub.3 H.sub.7 (iso)                                                                C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2   19.2 19.1                 521.             --NH.sub.2    --NH.sub.2  C.sub.13 H.sub.14 N.sub.4                                                                23.2 23.6                 522.                                                                               "            --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.15 H.sub.18 N.sub.4                                                                20.7 20.9                 523.             --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                   C.sub.19 H.sub.26 N.sub.4                                                      O.sub.3   15.7 16.2                     CH.sub.3                                                                   524.                                                                               --CO--N|                                                                           --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.16 H.sub.20 N.sub.4                                                                19.7 19.5                 525.                                                                               --SO.sub.2 --CH.sub.2 --CH.sub.3                                                            --NH--CH.sub.3                                                                               --NH--CH.sub.2 --CH.sub.3                                                                  C.sub.11 H.sub.19 N.sub.3                                                      O.sub.3 S 15.4 15.2                 526.                                                                               --SO.sub.2 --C.sub.3 H.sub.7 (n)                                                            --NH--C.sub.3 H.sub.7 (n) C.sub.15 H.sub.27 N.sub.3                                                      O.sub.3 S 12.8 13.1                 527.                                                                               --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                            --NH.sub.2    --NH.sub.2  C.sub.10 H.sub.17 N.sub.3                                                      O.sub.2 S 17.3 17.6                 528.                                                                               --SO.sub.2 --C.sub.4 H.sub.9 (iso)                                                          --NH.sub.2    --NH.sub.2  C.sub.10 H.sub.17 N.sub.3                                                      O.sub.2 S 17.3 17.4                                                CH.sub.3                                        529.                                                                               --SO.sub.2 --C.sub.5 H.sub.11 (iso)                                                         --NH--CH.sub.3                                                                               --N∠  C.sub.14 H.sub.25 N.sub.3                                                      O.sub.2 S 14.0 14.3                                                CH.sub.3                                        530.             --NH--CH.sub.3                                                                               "           C.sub.15 H.sub.25 N.sub.3                                                      O.sub.2 S 13.5 14.0                 531.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.14 H.sub.17 N.sub.3                                                      O.sub.2 S 14.4 14.2                 532.             --NHCH.sub.2 CH.sub.2 OH                                                                     --NH--CH.sub.3                                                                             C.sub.15 H.sub.18 ClN.sub.3                                                    O.sub.3 S 11.8 12.2                 533.                           --NH--CH.sub.3                                                                             C.sub.19 H.sub.25 N.sub.3                                                      O.sub.3 S 11.2 11.4                 534.                                                                               --SO.sub.2 --NH.sub.2                                                                       --NH.sub.2    --NH.sub.2  C.sub.6 H.sub.10 N.sub.4                                                       O.sub.2 S 27.7 27.5                 535.                                                                               --SO.sub.2 --NH.sub.2                                                                       --NH.sub.2                C.sub.12 H.sub.13 N.sub.3                                                      O.sub.4 S.sub.2                                                                          12.8 13.2                 536.                                                                               --SO.sub.2 --NH.sub.2                                                                       --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.8 H.sub.14 N.sub.4                                                       O.sub.2 S 24.4 24.2                 537.                                                                               --SO.sub.2 --NH.sub.2                                                                       --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                   C.sub.10 H.sub.18 N.sub.4                                                      O.sub.4 S 19.3 19.5                     CH.sub.3                                                                   538.                                                                               --SO.sub.2 --N∠                  C.sub.20 H.sub.22 N.sub.4                                                      O.sub.2 S 14.7 15.2                     CH.sub.3                                                                   539.                                                                               --SO.sub.2 NHC.sub.2 H.sub.5                                                                --NH--CH.sub.3            C.sub.15 H.sub.25 N.sub.3                                                      O.sub.2 S.sub.2                                                                          12.2 12.4                                                CH.sub.3                                        540.                                                                               --SO.sub.2 NH(CH.sub.2).sub.3 OCH.sub.3                                                     --NH.sub.2    --NH--N∠                                                                             C.sub.12 H.sub.23 N.sub.5                                                      O.sub.3 S 22.1 22.5                                                CH.sub.3                                        541.             --NH.sub.2    --NH.sub.2  C.sub.10 H.sub.16 N.sub.4                                                      O.sub.3 S 20.6 21.1                 542.                                                                               "            --NH--CH.sub.3            C.sub.15 H.sub.24 N.sub.4                                                      O.sub.4 S 15.7 16.0                                  C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 543.                                                                               "            --N∠    --N∠  C.sub.18 H.sub.32 N.sub.4                                                      O.sub.3 S 14.6 14.8                 544.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.13 H.sub.22 N.sub.4                                                      O.sub.2 S 18.8 18.5                 545.                                                                               "            --NH--CH.sub.3            C.sub.19 H.sub.25 N.sub.3                                                      O.sub.2 S.sub.2                                                                          10.7 11.2                 546.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.12 H.sub.23 N.sub.5                                                      O.sub.2 S 23.2 23.0                 547.                           --NH--CH.sub.3                                                                             C.sub.14 H.sub.24 N.sub.4                                                      O.sub.2 S 17.9 18.2                 548.                                                                               "            --NH--CH.sub.3            C.sub.19 H.sub.31 N.sub.3                                                      O.sub.4 S.sub.2                                                                          9.8  10.2                 549.                           --NHCH.sub.2 CH.sub.2 OH                                                                   C.sub.19 H.sub.26 N.sub.4                                                      O.sub.4 S 13.8 13.5                 550.             --NH.sub.2    --NH.sub.2  C.sub.12 H.sub.14 N.sub.4                                                      O.sub.2 S 20.1 20.3                 551.                                                                               "                                      C.sub.24 H.sub.34 N.sub.4                                                      O.sub.2 S 12.7 12.5                 552.                                                                               "                                      C.sub.26 H.sub.26 N.sub.4                                                      O.sub.2 S 12.2 12.5                 553.                                       C.sub.24 H.sub.22 N.sub.4                                                      O.sub.2 S 13.0 13.2                 554.                                                                               "                                      C.sub.32 H.sub.26 N.sub.4                                                      O.sub.2 S 10.6 10.2                                                CH.sub.3                                                                       |                                      555.                                                                               HC------CH   --NH--CH.sub.3                                                                               --OCh.sub.2 C=CH.sub.2                                                                     C.sub.16 H.sub.18 N.sub.2                                                      O.sub.3   9.8  9.5                      ∥∥                                                           --OC--CCH                                                                      ∠                                                                        O                                                                                                         CH.sub.3                                        556.                                                                               "            --NH--CH.sub.3                                                                               --NH(CH.sub.2).sub.3 --N∠                                                            C.sub.17 H.sub.24 N.sub.4                                                      O.sub.2   17.8 18.2                                                CH.sub.3                                        557.                                                                               HC------CH   --NH--CH.sub.3            C.sub.19 H.sub.24 N.sub.2                                                      O.sub.3   8.5  9.0                      ∥∥                                                           --OC--OCH                                                                      ∠                                                                        S                                                                          558.             --NH.sub.2    --NH.sub.2  C.sub.12 H.sub.12 N.sub.4                                                                24.5 25.0                 559.                                                                               "            --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.14 H.sub.16 N.sub.4                                                                21.8 22.2                                  CH.sub.3      CH.sub.3                                        560.                                                                               "            --N∠    --N∠  C.sub.16 H.sub.20 N.sub.4                                                                19.7 20.1                                  CH.sub.3      CH.sub.3                                        561.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.16 H.sub.17 N.sub.5                                                                23.7 23.5                                  CH.sub.3      CH.sub.3                                        562.                                                                               "            --N∠    --N∠  C.sub.18 H.sub.21 N.sub.5                                                                21.7 21.5                                  CH.sub.3      CH.sub.3                                        563.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.16 H.sub.16 N.sub.4                                                                17.9 18.2                                  CH.sub.3      CH.sub.3                                        564.             --N∠    --N∠  C.sub.19 H.sub.22 N.sub.4                                                      O.sub.2 S 15.1 15.5                                  CH.sub.3      CH.sub.3                                        565.                                                                               HC------C--CH.sub.3                                                                         --NH--CH.sub.3                                                    ∥∥                                                           --OC--CCH                              C.sub.20 H.sub.19 ClN.sub.2                                                    O.sub.2 S 7.3  7.0                      ∠                                                                        S                                                                          566.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.14 H.sub.18 N.sub.4                                                                23.1 23.5                 567.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.14 H.sub.18 N.sub.4                                                                23.1 23.3                 568.             --NH--CH.sub.3                                                                               --NH--CH.sub.3                                                                             C.sub.15 H.sub.20 N.sub.4                                                                21.9 21.7                                                CH.sub.3                                        569.                                                                               --C.sub.4 H.sub.9 (n)                                                                       --CN          --N∠  C.sub.13 H.sub.19 N.sub.3                                                                19.4 19.0                                                CH.sub.3                                        570.                                                                               --CO--NH.sub.2                                                                              --OCH.sub.3   --OCH.sub.3 C.sub.9 H.sub.12 N.sub.2                                                       O.sub.3   14.3 14.7                 571.                                                                               --CO--CH.sub.3                                                                              --OC.sub.2 H.sub.5                                                                           --OC.sub.2 H.sub.5                                                                         C.sub.12 H.sub.17 NO.sub.3                                                               6.7  6.5                  __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the method of this invention: ##SPC31##

or tautomeric forms.

    __________________________________________________________________________                                            Empirical                                                                             Cal'd                                                                               Found                       No. Y              Z.sub.1   Z.sub.2   Formula                                                                               N%   N%                          __________________________________________________________________________     572.                                                                               --H            --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.8 H.sub.10 N.sub.4                                                              34.6 25.0                        573.                                                                               --H            --NH--CH.sub.2 --CH.sub.2 --OH                                                                     C.sub.10 H.sub.14 N.sub.4 O.sub.2                                                     25.2 25.0                                           CH.sub.3                                                    574.                                                                               --C.sub.3 H.sub.7 (n)                                                                         --NHCH.sub.2 CH.sub.2 CH.sub.3 --NH(CH.sub.2).sub.3                            N∠            C.sub.17 H.sub.29 N.sub.5                                                             23.1 23.3                                           CH.sub.3                                                                       CH.sub.3                                                    575.                                                                               --C.sub.3 H.sub.7 (iso)                                                                       --NHCH.sub.2 CH.sub.2 CH.sub.3 --NH(CH.sub.2).sub.3                            N∠            C.sub.17 H.sub.29 N.sub.5                                                             23.1 22.8                                           CH.sub.3                                                    576.                                                                               --C.sub.6 H.sub.13 (n)                                                                        --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           C.sub.20 H.sub.34 N.sub.4 O.sub.2                                                     15.5 16.0                            CH.sub.3                                                                   577.                                                                               --CH.sub.2 CH.sub.2 N∠                                                                  --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.12 H.sub.19 N.sub.5                                                             30.0 30.3                            CH.sub.3                                                                       CO--CH.sub.3                                                               578.                                                                               --CH.sub.2 CH.sub.2 N∠                                                                  --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.13 H.sub.19 N.sub.5 O                                                           26.8 27.0                            CH.sub.3                                                                   579.               --NH.sub.2                                                                               --NH.sub.2                                                                               C.sub.12 N.sub.17 N.sub.5 O                                                           28.3 28.8                        580.               --NH.sub.2                                                                               --NH.sub.2                                                                               C.sub.12 H.sub.17 N.sub.5                                                             30.3 30.5                        581.                                                                               --CH.sub.2 CH.sub.2 OH                                                                        --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.10 H.sub.14 N.sub.4 O                                                           27.2 27.5                        582.                                                                               --CH.sub.2 CH.sub.2 O--COCH.sub.3                                                             --NHCH.sub.2 CH.sub.2 CH.sub.2 OH                                                                  C.sub.16 H.sub.24 N.sub.4 O.sub.4                                                     16.7 17.0                        583.                                                                               --(CH.sub.2).sub.2 O--CONHC.sub.2 H.sub.5                                                     --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.13 H.sub.19                                                                     25.3b.5 O.sub.2                                                                     25.1                        584.               --NH(CH.sub.2).sub.3 O--C.sub.3 H.sub.7 (iso)                                                      C.sub.26 H.sub.38 N.sub.4 O.sub.3                                                     12.3 12.7                        585.               --NH.sub.2                                                                               --NH.sub.2                                                                               C.sub.12 H.sub.16 N.sub.4                                                             25.9 25.5                        586.               --NH.sub.2                                                                               --NH.sub.2                                                                               C.sub.13 H.sub.12 N.sub.4                                                             25.0 25.3                        587.                         --NH--CH.sub.3                                                                           C.sub.17 H.sub.18 N.sub.4                                                             20.1 20.7                        588.               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.14 H.sub.13 N.sub.4 Cl                                                          20.6 21.0                        589.               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.16 H.sub.18 N.sub.4                                                             21.0 20.4                        590.                                                                               HC----CH       --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.12 H.sub.12 N.sub.4 O                                                           24.5 24.7                            ∥∥                                                           --CCH                                                                          ∠                                                                        O                                                                          591.                                                                               HC----CH       --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.12 H.sub.12 N.sub.4 S                                                           22.9 22.5                            ∥∥                                                           --CCH                                                                          ∠                                                                        N----CH                                                                    592.                                                                               ∥∥                                                                          --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.11 H.sub.11 N.sub.5 S                                                           28.6 28.5                            --CCH                                                                          ∠                                                                        S                                                                          593.               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.14 H.sub.15 N.sub.5                                                             27.7 28.2                        594.               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.13 H.sub.13 N.sub.5                                                             28.3 28.7                        595.               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.15 H.sub.14 N.sub.6                                                             30.2 29.6                            N--CH                                                                      596.                                                                               --H.sub.2 C--C∠∥                                                               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                           C.sub.12 H.sub.13 N.sub.5 S                                                           27.0 27.3                            S--CH                                                                      597.               --NH--C.sub.2 H.sub.5                                                                    --NH--C.sub.2 H.sub.5                                                                    C.sub.17 H.sub.18 N.sub.6                                                             27.5 27.7                                                     CH.sub.3                                          598.                                                                               --C.sub.3 H.sub.7 (n)                                                                         --CN      --N∠                                                                               C.sub.12 H.sub.14 N.sub.4                                                             26.2 26.5                                                     CH.sub.3                                          599.                                                                               --C.sub.3 H.sub.7 (n)                                                                         --SCH.sub.3                                                                              --OCH.sub.3                                                                              C.sub.11 H.sub.14 N.sub.2 OS                                                          12.6 13.0                        __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the method of this invention: ##SPC32##

or tautomeric forms.

    __________________________________________________________________________                                                     Empirical                                                                             Cal'd.                                                                             Found               No.                                                                               X          Y          Z.sub.1    Z.sub.2     Formula                                                                               N%  N%                  __________________________________________________________________________                                         CH.sub.3                                   600.                                                                              --C.sub.3 H.sub.7 (n)                                                                     --C.sub.4 H.sub.9 (n)                                                                     --CN       --N∠  C.sub.15 H.sub.23                                                                     17.1b.3                                                                            17.5                                                    CH.sub.3                                   601.                                                                              --C.sub.3 H.sub.7 (n)                                                                     --CN       --OCH.sub.3                                                                               "           C.sub.12 H.sub.17 N.sub.3                                                      O      18.7                                                                               19.2                602.                                                                              --C.sub.3 H.sub.7 (n)                                                                     --C.sub.3 H.sub.7 (n)                                                                     --SCH.sub.3                                                                               --SCH.sub.3 C.sub.13 H.sub.21                                                              NS.sub.2                                                                               5.5                                                                                5.8                603.                                                                              H          --CH.sub.3 --NH.sub.2 --NH.sub.2  C.sub.6 H.sub.9 N.sub.3                                                               34.1                                                                               34.5                604.                                                                              H                     --NH--CH.sub.3                                                                            --NH--CH.sub.3                                                                             C.sub.13 H.sub.16                                                                     24.5b.4                                                                            24.2                                         CH.sub.3   CH.sub.3                                   605.                                                                              H          --CO--NH.sub.2                                                                            --N∠ --N∠  C.sub. 10 H.sub.16                                                             N.sub.4 O                                                                             26.9                                                                               27.3                                         CH.sub.3   CH.sub.3                                                                       CH.sub.3                                                                       |                                 606.                                                                              --C.sub.2 H.sub.5                                                                         --NH.sub.2 --NH--CH.sub.3                                                                            --OCH.sub.2 C=CH.sub.2                                                                     C.sub.12 H.sub.19 N.sub.3                                                      O      19.0                                                                               19.2                607.                                                                              --C.sub.2 H.sub.5                                                                         --H        --NHCH.sub.2 CH.sub.2 OH                                                                              C.sub.13 H.sub.21 N.sub.3                                                      O      17.9                                                                               18.2                608.                                                                              --C.sub.4 H.sub.9 (n)                                                                     --NO       --NH--CH.sub.3                                                                            --NH--CH.sub.3                                                                             C.sub.11 H.sub.18 N.sub.4                                                      O      25.2                                                                               25.0                609.                                                                              --C.sub.4 H.sub.9 (n)                                                                     --NO.sub.2 --NH--CH.sub.3                                                                            --NH--CH.sub.3                                                                             C.sub.11 H.sub.18 N.sub.4                                                      O.sub.2                                                                               23.5                                                                               23.2                610.                                                                              --C.sub.4 H.sub.9 (n)                                                                     --C.sub.4 H.sub.9 (n)                                                                     --NH.sub.2             C.sub.20 H.sub.28 N.sub.2                                                      O.sub.2                                                                                8.5                                                                                8.2                611.                                                                              --C.sub.4 H.sub.9 (sec)                                                                              --NH--C.sub.2 H.sub.5  C.sub.19 H.sub.28                                                                     17.9b.4                                                                            17.6                              N----CH    C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                            612.                                                                              --C.sub.4 H.sub.9 (sec)                                                                   ∥∥                                                                      --N∠ --N∠  C.sub.20 H.sub.32 N.sub.4                                                      S      15.5                                                                               16.1                              --CCH      C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                          ∠                                                                        S                                                                613.                                                                              --C.sub.4 H.sub.9 (iso)                                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                       C.sub.21 H.sub.30 N.sub.4                                                      O.sub.3                                                                               14.5                                                                               14.2                614.                                                                              --C.sub.4 H.sub.9 (tert)                                                                  --CO--NH.sub.2                                                                            --NH--CH.sub.3                                                                            --SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     C.sub.14 H.sub.23 N.sub.3                                                      O.sub.4 S                                                                             12.8                                                                               12.2                615.                                                                              --C.sub.5 H.sub.11 (iso)                                                                  --CO--NH.sub.2                                                                            --NH--CH.sub.3         C.sub.19 H.sub.22 N.sub.4                                                      O.sub.3 S                                                                             14.5                                                                               14.3                                                    CH.sub.3                                   616.                                                                              --CH=CH.sub.2                                                                             --COOC.sub.2 H.sub.5  --N∠  C.sub.16 H.sub.23 N.sub.3                                                      O.sub.3                                                                               13.8                                                                               14.2                                                    CH.sub.3                                   617.                                                                              --CH=CH--CH.sub.3                                                                         --SO.sub.2 --NH.sub.2             C.sub.20 H.sub.20 N.sub.4                                                      O.sub.2 S                                                                             14.7                                                                               15.2                   C.sub.2 H.sub.5                                                             618.                                                                              --CH.sub.2 CH.sub.2 N∠                                                              --CH.sub.3 --NH--CH.sub.3                                                                            --NH--CH.sub.3                                                                             C.sub.14 H.sub.26                                                                     22.4b.4                                                                            22.8                   C.sub.2 H.sub.5                                                                           CH.sub.3                                                         619.                                                                              --CH.sub.2 CH.sub.2 CN                                                                    --CH.sub.2 CH.sub.2 N∠                                                                         --NH--CH.sub.3                                                                             C.sub.17 H.sub.27 N.sub.5                                                      O      22.1                                                                               22.5                620.                                                                              --CH.sub.2 CH.sub.2 OCH.sub.3                                                             --CO--CH.sub.3                                                                            --NHCH.sub.2 CH.sub.2 CH.sub.3                                                            --SCH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.16 H.sub.26 N.sub.2                                                      O.sub.3 S                                                                              8.6                                                                                8.9                621.          --H        --NH(CH.sub.2).sub.3 --OCH.sub.3                                                          --NH(CH.sub.2).sub.3 --OCH.sub.3                                                           C.sub.20 H.sub.36 N.sub.4                                                      O.sub.2                                                                               15.4                                                                               15.6                                                    C.sub.2 H.sub.5                            622.          --CO--NH.sub.2        --N∠  C.sub.21 H.sub. 37                                                             N.sub.5 O                                                                             18.7                                                                               18.5                                                    C.sub.2 H.sub.5                            623.          --CH.sub.2 --OCH.sub.3                                                                    --NH.sub.2 --NH.sub.2  C.sub.13 H.sub.21 N.sub.3                                                      O      17.9                                                                               17.6                624.          --H                               C.sub.23 H.sub.19                                                                     12.5b.3                                                                            12.7                                         CH.sub.3                                              625.                                                                              "          --CO--NH.sub.2                                                                            --N∠             C.sub.22 H.sub.23 N.sub.3                                                      O.sub.3 S                                                                             10.3                                                                               10.7                                         CH.sub.3                                              626.                                                                              "          --CO--CH.sub.3                                                                            "                      C.sub.23 H.sub.21 N.sub.3                                                      O.sub.2 S                                                                             10.4                                                                               10.6                627.          --H        --NH--CH.sub.3                                                                            --NH--CH.sub.3                                                                             C.sub.12 H.sub.14                                                                     26.2b.4                                                                            26.8                                         CH.sub.3   CH.sub.3                                   628.                                                                              "          --CO--NH.sub.2                                                                            --N∠ --N∠  C.sub.15 H.sub.19 N.sub.5                                                      O      24.6                                                                               25.0                                         CH.sub.3   CH.sub.3                                   629.                                                                               N----CH   --CO--NH.sub.2                                                                            --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                       C.sub.15 H.sub.21 N.sub.5                                                      O.sub.3 S                                                                             20.0                                                                               20.3                   ∥∥                                                           --CCH                                                                          ∠                                                                        S                                                                           630.          --CO--NH.sub.2                                                                            --NH.sub.2 --OH        C.sub.13 H.sub.10 N.sub.4                                                      O.sub.2 S                                                                             19.6                                                                               19.4                __________________________________________________________________________

In those instances in the foregoing tables where only one value is presented for Z₁ and Z₂, this means that Z₁ and Z₂ are equal.

EXAMPLE 13

There are allowed to run 100 p.b.w. 3-methoxypropylamine into a suspension of 93.0 p.b.w. of 2,6-dichloro-3-cyano-4-methylpyridine in 200 p.b.w. ethyl alcohol for 2 hours at 20°C. This product is then agitated at room temperature for 18 hours. Then the resulting 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine of the formula ##SPC33##

is drawn off, washed on the suction apparatus first with 120 p.b.w. ethyl alcohol and subsequently with water. The substance is analytically pure.

Analysis: C₁₁ H₁₄ ClN₃ O -- Calculated: 17.6% N, 14.6% Cl. Found: 17.9% N, 14.4% Cl.

EXAMPLE 14

Introduced into 1000 parts by weight methyl alcohol during cooling are 25.3 p.b.w. sodium. Added to this sodium methylate solution are 215 p.b.w. 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine, and subsequently the reaction solution is heated to the point of boiling for 24 hours under reflux. Then the methyl alcohol is distilled off and the residue stirred with water. The resulting 2-methoxy-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine of the formula ##SPC34##

is an oil, which is isolated with ether. It may be purified by vacuum distillation.

Analysis: C₁₂ H₁₇ N₃ O₂ -- Calculated: 17.9% N, 26.4% --OCH₃. Found: 18.1% N, 26.1% --OCH₃.

EXAMPLE 15

a. 13.8 p.b.w. 4-nitraniline are diazotized at 0° to +5°C. in 300 p.b.w. of water to which 36.0 p.b.w. hydrochloric acid of 30 % have been added, with a solution consisting of 7.7 p.b.w. sodium nitrite in 50 p.b.w. of water. The filtered diazo solution is allowed to run into a solution of 500 p.b.w. of water, 25.0 p.b.w. hydrochloric acid of 30 % and 32.2 p.b.w. 2.6-bis-(3'-methoxy-n.propylamino)-3-cyano-4-methyl-pyridine, whereby the reaction temperature is maintained during the coupling at 0° to +5°C. by the addition of 500 parts of ice. The pH value of the batch is neutralized by the introduction of a solution of 65.2 p.b.w. sodium acetate in 200 p.b.w. of water, whereupon the coupling is quickly completed. The dyestuff being formed is then sucked off, washed with water until neutral and dried.

b. 1.0 g. of the dyestuff thus obtained which has the following formula ##SPC35##

is finely dispersed and introduced while stirring into 2000 g. of water. This reaction mixture is adjusted to a pH value of 5 - 6 by the addition of acetic acid and then admixed with 4 g. ammonium sulfate and 2 g. of a commercial dispersing agent on the basis of a naphthalenesulfonic acid/formaldehyde condensation product. 100 g. of a polyester fabric on the basis of polyethylene glycolterephthalate are introduced into the dye liquor thus obtained and dyed for 1 1/2 hours at 130°C. After subsequent rinsing, reductive aftertreatment with an alkaline sodium dithionite solution of 0.2 % during 15 minutes at 60° - 70°C., rinsing and drying, one obtains a deep reddish orange dyeing which shows very good fastness properties.

EXAMPLE 16

a. 16.3 p.b.w. 2-cyano-4-nitraniline are diazotized at 15°C. in 100 p.b.w. glacial acetic acid, with 34.2 p.b.w. nitrosylsulfuric acid of 41.3 %. The limpid diazo solution is then allowed to run into a suspension of 25.8 p.b.w. 2-methoxy-3-cyano-4-methyl-6-(3'-methoxy-propylamino)-pyridine and 66.0 g. sodium acetate in 160 p.b.w. ethanol. During the coupling the reaction temperature is maintained at 0 to +5°C. by cooling from the outside. When the coupling is completed, the dyestuff being formed is sucked off, washed first with ethanol, then with water and dried.

b. 30 p.b.w. of the dyestuff thus obtained (related to 1000 p.b.w. of the printing paste) which has the formula ##SPC36##

are incorporated in a finely dispersed form into a printing paste containing 45.0 p.b.w. carob bean meal, 6.0 p.b.w. 3-nitrobenzenesulfonic acid sodium and 3.0 p.b.w. citric acid. When this printing paste is applied onto a polyester fabric one obtains after printing, drying and setting on the thermosetting stenter during 45 seconds at 215°C., rinsing and working up as described in the above Example 15 (b), a full reddish orange print which has very good fastness properties.

The dyestuff yields when printed onto a triacete fabric and if it is employed in the form of the above printing paste and the printed fabric, after drying, is steamed for 10 minutes at a pressure of 2.5 atmospheres, rinsed, soaped, rinsed again and dried, a full reddish orange print having also very good fastness properties.

EXAMPLE 17

a. 29.7 g. 4-β-sulfatoethylsulfonyl-aniline-2-sulfonic acid are pasted up with 400 c.c. water, admixed with 25 c.c. 10 normal hydrochloric acid and diazotized by the addition of 100 c.c. 4 normal sodium dithionite solution. The reaction temperature is maintained at 0° to +3°C. by the addition of about 400 g. ice. The excess sodium, if any, is destroyed with little amidosulfonic acid and the diazo compound is added to a suspension of 14.8 g. 2.6-diamino-3-cyano-4-methyl-pyridine in 200 c.c. water to which 12.5 g. sodium bicarbonate have been added. The precipitated dyestuff is sucked off, and dried in vacuo. The reactive dye thus obtained has the following formula: ##SPC37##

b. A mixture of mercerized or alkalized cotton is printed with the following printing paste:50 g. of the above dyestuff100 g. urea370 g. hot water450 g. alginate thickener20 g. sodium bicarbonate10 g. sodium salt of the m-nitrobenzenesulfonic acid1000 g.

The print may be fixed either by steaming at 103° to 105°C. or by dry heating. In both cases the fabric is subsequently rinsed and soaped. The full greenish yellow print thus obtained has very good fastness properties.

Cationic azo dyes suited for dyeing and printing polyacrylonitrile and modified polyester fibers may be prepared according to the following Example:

EXAMPLE 18

a. 4.57 p.b.w. 4'aminophenacyltrimethyl-ammonium chloride are dissolved in 20 p.b.w. of water and 7 p.b.w. concentrated hydrochloric acid, and diazotized at 0° - 5°C. with 4 p.b.w. 5 normal sodium nitrite solution. When the diazotization is completed, 3.52 p.b.w. 3-cyano-4-methyl-2.6-bis-methylamino-pyridine, dissolved in 10 p.b.w. glacial acetic acid, are added to the diazo solution and the reaction mixture is stirred at a pH value of 3 - 5 until the coupling is completed.

The dyestuff is precipitated by the addition of sodium chloride of 10 %, sucked off and dried. It has the following formula: ##SPC38##

b. 1 g. of this dyestuff is pasted up with 2.5 g. acetic acid of 50 % and dissolved in 6 l. of water. To this dye liquor 1 g. sodium acetate and 10 g. sodium sulfate are added. Subsequently, 100 g. of a pre-washed polyacrylonitrile staple fiber yarn are introduced into the dye liquor which has a temperature of 60°C. This temperature is slowly raised to 100°C. and dyeing is carried out during 1 hour at boiling temperature. Subsequently, the temperature is lowered down to 70°C., the treated fabric is rinsed and dried. One obtains a clear deep orange dyeing with a very good fastness to light and to wetting, and a high absorption capacity.

c. 1 g. of the dyestuff is pasted up with 2 g. acetic acid of 50 % and dissolved in 5 l. of water which contains 1 g. sodium acetate, 100 g. of a pre-washed fabric of acid modified polyester fiber are then introduced at 60°C., the temperature is slowly raised and dyeing is carried out during 1 hour at 115°C. The temperature is then lowered down to 70°C. and the fabric is rinsed and dried. Obtained is a deep orange dyeing having a very good fastness to light and wetting.

Acid azo dyes which are suited for dyeing wool, silk and polyamide may be prepared according to the following Example:

EXAMPLE 19

a. 27.7 p.b.w. 4'-amino-azobenzene-4-sulfonic acid are diazotized in the usual manner and coupled in a slightly acid pH range with 23.6 p.b.w. 2.6-(β-hydroxyethylamino)-3-cyano-4-methyl-pyridine. The dyestuff being formed is salted out by the addition of sodium chloride of 10 %, sucked off and dried at 60°C. in vacuo. In the form of its free acid it corresponds to the following formula: ##SPC39##

b. 1 g. of the above dyestuff is pasted up with 25 g. cold distilled water and dissolved in 975 g. boiling distilled water. The dyestuff solution is admixed with 2 g. acetic acid of 50 % and the reaction temperature is maintained at 60°C. At this temperature 100 g. of a pre-washed fabric of wool, silk or polyamide are introduced and the temperature is slowly raised to 100°C. and then maintained for 1 hour at boiling temperature. Subsequently, the temperature is lowered down to 70°C. and the fabric is rinsed and dried. Obtained is a deep yellowish red dyeing of high brilliancy and showing a very good fastness to light and to wetting. 

We claim:
 1. A compound of the formula ##SPC40##wherein X is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl or phenethyl; Z₁ is ##EQU25## -NH-OR₁₀ or ##EQU26## R₅ and R₆ are hydrogen, alkyl having one to six carbon atoms, hydroxyalkyl having one to six carbon atoms, cycloalkyl having three to eight carbon atoms, methoxyalkyl or ethoxyalkyl having one to six carbon atoms in the alkyl moiety, benzyl or phenethyl; R₁₀ is alkyl having one to six carbon atoms, benzyl or phenethyl; R₁₁ is alkyl having one to six carbon atoms and R₁₂ is alkyl having one to six carbon atoms, alkenyl having two to six carbon atoms, cycloalkyl having three to eight carbon atoms, phenyl, benzyl or phenethyl.
 2. The compounds of claim 1 wherein X is methyl. 